N-biphenylamides and fungicidal compositions containing the same

ABSTRACT

A N-biphenylamide compound of the formula (1):  
                 
 
wherein R 1 , R 2 , R 3 , R 4  and R 5  independently represent a hydrogen atom, halogen atom or the like, R 6  represents C1-C6 alkyl and the like, R 7  represents a hydrogen atom or C1-C3 alkyl, 
         R 8  represents a hydrogen atom or C1-C3 alkyl,    R 9  and R 10  independently represents a halogen atom, C1-C6 alkyl, C1-C6 alkoxy or the like,    R 11 , R 12  and R 13  independently represent a hydrogen atom, halogen atom or the like, R 14 , R 15 , R 16  and R 17  independently is a hydrogen atom, halogen atom or the like, X 1  represents an oxygen atom or sulfur atom, X 2  represents an oxygen atom or sulfur atom; has excellent effect aginst plant diseases.

TECHNICAL FIELD OF THE INVENTION

The present invention relates to N-biphenylamide compounds andfungicidal compositions containing the same.

BACKGROUND ART

Some of N-biphenylamide compounds are disclosed in International PatentApplication published under the Patent Cooperation Treaty WO97/08148,European Patent Published Application 0545099 and the like.

The object of the present invention is to provide a novelN-biphenylamide compound having excellent controlling activity againstplant diseases.

DISCLOSURE OF THE INVENTION

The present inventor has earnestly studied, and found that theN-biphenylamide compound of the formula (1) has excellent plant diseasescontrolling effect to complete the present invention.

Namely, the present invention provides the N-biphenylamide compound(hereinafter, referred to as the present compound) of the followingformula (1):

wherein R¹, R², R³, R⁴ and R⁵ independently represent a hydrogen atom,halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6haloalkenyl, C2-C6 alkynyl, C2-6 haloalkynyl, C1-C6 alkoxy, C1-C6haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy,C3-C6 haloalkynyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C6cycloalkyl, C3-C6 cycloalkoxy, tri(C1-C6 alkyl)silyl or cyano,

-   -   R⁶ represents C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6        haloalkenyl, C3-6 alkynyl, C3-C6 haloalkynyl, (C1-C6        alkyl)carbonyl, (C1-C6 haloalkyl)carbonyl, (C2-C6        alkenyl)carbonyl, (C2-C6 haloalkenyl)carbonyl, (C2-C6        alkynyl)carbonyl or (C2-C6 haloalkynyl)carbonyl,    -   R⁷ represents a hydrogen atom or C1-C3 alkyl,    -   R⁸ represents a hydrogen atom or C1-C3 alkyl,    -   R⁹ and R¹⁰ independently represents a halogen atom, C1-C6 alkyl,        C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6        alkynyl, C2-C6 haloalkynyl, cyano C1-C6 alkyl, C1-C6 alkoxy,        C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6        alkynyloxy, C3-C6 haloalkynyloxy, cyano C1-C6 alkoxy, C1-C6        alkylthio, C1-C6 haloalkylthio, C3-C6 alkenylthio, C3-C6        alkynylthio, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, (C3-C6        cycloalkyl) C1-C3 alkoxy, C2-C6 alkoxyalkyl, tri(C1-C6        alkyl)silyl or cyano,    -   R¹¹, R¹² and R¹³ independently represent a hydrogen atom,        halogen atom or C1-C3 alkyl,    -   R¹⁴, R¹⁵, R¹⁶ and R¹⁷ independently is a hydrogen atom, halogen        atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6        haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy,        C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6        alkynyloxy, C3-C6 haloalkynyloxy, C1-C6 alkylthio, C1-C6        haloalkylthio, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, tri(C1-C6        alkyl)silyl or cyano,    -   X¹ represents an oxygen atom or sulfur atom,    -   X² represents an oxygen atom or sulfur atom;        -   the fungicidal composition comprising the present compound            as an active ingredients; and the method for controlling            plant diseases comprising applying the present compound to            the plant or the soil.

In the present invention, a specific example of each substituent in theformula (1) is shown in the following.

In R¹, R², R³, R⁴ and R⁵;

-   -   the halogen atom includes, for example, a fluorine atom,        chlorine atom and bromine atom;    -   the C1-C6 alkyl includes, for example, methyl, ethyl, propyl,        isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,        isopentyl and hexyl;    -   the C1-C6 haloalkyl includes, for example, fluoromethyl,        difluoromethyl, trifluoromethyl, chlorodifluoromethyl,        chlorofluoromethyl, bromodifluoromethyl, trichloromethyl,        dichlorobromomethyl, 1,1,2,2,2-pentafluoroethyl,        2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl and        6,6,6-trifluorohexyl;    -   the C2-C6 alkenyl includes, for example, vinyl, 2-propenyl,        1-methyl-2-propenyl,    -   2-methyl-2-propenyl, 2-butenyl, 3-butenyl, 2-hexenyl and        5-hexenyl;    -   the C2-C6 haloalkenyl includes, for example, 1-chlorovinyl,        2-chlorovinyl, 2,2-dichlorovinyl, 2,2-difluorovinyl,        1,2-dichlorovinyl, 3,3-dichloro-2-propenyl and        3,3-difluoro-2-propenyl;    -   the C2-C6 alkynyl includes, for example, ethynyl, 3-butynyl,        3-hexynyl and 5-hexynyl;    -   the C2-C6 haloalkynyl includes, for example, 2-chloroethynyl,        2-bromoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl and        6-chloro-5-hexynyl;    -   the C1-C6 alkoxy, for example, methoxy, ethoxy, propoxy,        isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy,        pentyloxy, isopentyloxy and hexyloxy;    -   the C1-C6 haloalkoxy includes, for example, trifluoromethoxy,        difluoromethoxy, bromodifluoromethoxy, chlorodifluoromethoxy,        fluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy,        5-chloropentyloxy, 4-fluoroisopentyloxy and        2,2-dichlorohexyloxy;    -   the C3-C6 alkenyloxy includes, for example, 2-propenyloxy,        1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy,        3-butenyloxy, 2-hexenyloxy and 5-hexenyloxy;    -   the C3-C6 haloalkenyloxy includes, for example,        3,3-dichloro-2-propenyloxy, 3,3-difluoro-2-propenyloxy,        3,3-dibromo-2-propenyloxy, 2,3-dichloropropenyloxy,        6-fluoro-2-hexenyloxy and 2,2-dichloro-5-hexenyloxy;    -   the C3-C6 alkynyloxy includes, for example, 2-propynyloxy,        1-methyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 2-hexynyloxy        and 5-hexynyloxy;    -   the C3-C6 haloalkynyloxy includes, for example,        3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy,        3-iodo-2-propynyloxy and 6-chloro-5-hexynyloxy;    -   the C1-C6 alkylthio includes, for example, methylthio,        ethylthio, propylthio, isopropylthio, butylthio, isobutylthio,        sec-butylthio, tert-butylthio, pentylthio, isopentylthio and        hexylthio;    -   the C1-C6 haloalkylthio includes, for example,        trifluoromethylthio, difluoromethylthio,        bromodifluoromethylthio, chlorodifluoromethylthio,        fluoromethylthio, 2,2,2-trifluoroethylthio,        1,1,2,2-tetrafluoroethylthio, 5-chloropentylthio,        4-fluoroisopentylthio and 2,2-dichlorohexylthio;    -   the C3-C6 cycloalkyl includes, for example, cyclopropyl,        cyclopentyl and cyclohexyl;    -   the C3-C6 cycloalkoxy includes, for example, cyclopropoxy,        cyclobutoxy, cyclopentoxy and cyclohexyloxy;    -   the tri(C1-C6 alkyl)silyl includes, for example, trimethylsilyl,        triethylsilyl, tributylsilyl and tert-butyldimethylsilyl.

The phenyl substituted with R¹, R², R³, R⁴ and R⁵ includes, for example,the phenyl wherein R¹, R² and R³ are independently a hydrogen atom,halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy,C3-C6 haloalkynyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C6cycloalkyl, C3-C6 cycloalkoxy, tri(C1-C6 alkyl)silyl or cyano, and R⁴and R⁵ are hydrogen atoms;

-   -   the phenyl wherein R¹ and R² are independently a hydrogen atom,        halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6        haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy,        C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6        alkynyloxy, C3-C6 haloalkynyloxy, C1-C6 alkylthio, C1-C6        haloalkylthio, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, tri(C1-C6        alkyl)silyl or cyano, and R³, R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a chlorine atom, R² is a fluorine atom,        and R³, R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ and R² are chlorine atoms, and R³, R⁴ and        R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a chlorine atom, R² is a bromine atom,        and R³, R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a chlorine atom, R² is methyl, and R³,        R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a chlorine atom, R² is methoxy, and R³,        R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a bromine atom, R² is a fluorine atom,        and R³, R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a bromine atom, R² is a chlorine atom,        and R³, R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ and R² are bromine atoms, and R³, R⁴ and        R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a bromine atom, R² is methyl, and R³,        R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a bromine atom, R² is methoxy, and R³,        R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is methyl, R² is a fluorine atom, and R³,        R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is methyl, R² is a chlorine atom, and R³,        R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is methyl, R² is a bromine atom, and R³,        R⁴ and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ and R² are methyl, and R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is methyl, R² is methoxy, and R³, R⁴ and        R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is a fluorine atom, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is a chlorine atom, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is a bromine atom, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is iodine atom, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is methyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is ethyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is propyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wehrein R¹ is isopropyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is fluoromethyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is difluoromethyl, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is trifluoromethyl, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is 2-fluoroethyl, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is 2,2-difluoroethyl, and R², R³, R⁴ and        R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is 2,2,2-trifluoroethyl, and R², R³, R⁴        and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is 1,2,2,2-tetrafluoroethyl, and R², R³,        R⁴and R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is pentafluoroethyl, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is vinyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is 1-methylvinyl, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is 1-propenyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is ethynyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is 1-propynyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is methoxy, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is ethoxy, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is propoxy, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is isopropoxy, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is fluoromethoxy, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is difluoroethoxy, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is trifluoroethoxy, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is methylthio, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is ethylthio, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is propylthio, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R¹ is isopropylthio, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is fluoromethylthio, and R², R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R¹ is difluoromethylthio, and R², R³, R⁴ and        R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is trifluoromethylthio, and R², R³, R⁴ and        R⁵ are hydrogen atoms;    -   the phenyl wherein R¹ is cyclopropyl, and R², R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R² is a fluorine atom, and R¹, R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R² is a chlorine atom, and R¹, R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R² is a bromine atom, and R¹, R³, R⁴ and R⁵        are hydrogen atoms;    -   the phenyl wherein R² is methyl, and R¹, R³, R⁴ and R⁵ are        hydrogen atoms;    -   the phenyl wherein R² is methoxy, and R¹, R³, R⁴ and R⁵ are        hydrogen atoms; and    -   the phenyl wherein R¹, R², R³, R⁴ and R⁵ are hydrogen atoms.

In R⁶;

-   -   the C1-C6 alkyl includes, for example, methyl, ethyl, propyl,        isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,        isopentyl and hexyl;    -   the C1-C6 haloalkyl includes, for example, fluoromethyl,        difluoromethyl, bromodifluoromethyl, chlorofluoromethyl,        bromodifluoromethyl, 2,2,2-trifluoroethyl;    -   2,2-difluoroethyl, 2-fluoroethyl and 6,6,6-trifluorohexyl;    -   the C3-C6 alkenyl includes, for example, 2-propenyl,        1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl,        2-hexenyl and 5-hexenyl;    -   the C3-C6 haloalkenyl includes, for example,        3,3-dichloro-2-propenyl and 3,3-difluoro-2-propenyl;    -   the C3-C6 alkynyl includes, for example, a 2-propynyl,        1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 2-hexynyl and        5-hexynyl;    -   the C3-C6 haloalkynyl includes, for example,        3-chloro-2-propynyl, 3-bromo-2-propynyl and 6-chloro-5-hexynyl;    -   the (C1-C6 alkyl)carbonyl includes, for example, acetyl,        propionyl, butyryl, isobutyryl, valeryl, isovaleryl,        2-methylbutanoyl, pivaloyl, hexanoyl, 4-methylpentanoyl and        heptanoyl;    -   the (C1-C6 haloalkyl)carbonyl includes, for example,        fluoroacetyl, difluoroacetyl, bromodifluoroacetyl,        chlorofluoroacetyl, bromodifluoroacetyl,        3,3,3-trifluoropropanoyl, 3,3-difluoropropanoyl,        3-fluoropropanoyl and 7,7,7-trifluoroheptanoyl;    -   the (C2-C6 alkenyl)carbonyl includes, for example, acryloyl,        3-butenoyl, 2-methylbutenoyl, 3-methylbutenoyl, 3-pentenoyl,        4-pentenoyl, 3-heptenoyl and 6-heptenoyl;    -   the (C2-C6 haloalkenyl)carbonyl includes, for example,        4,4-dichloro-3-butenoyl and 4,4-difluoro-3-butenoyl;    -   the (C2-C6 alkynyl)carbonyl includes, for example, propioloyl,        3-butynoyl, 2-methyl-3-butynoyl, 3-pentynoyl, 4-pentynoyl,        3-heptynoyl and 6-heptynoyl;    -   the (C2-C6 haloalkynyl)carbonyl includes, for example,        4-chloro-3-butynoyl, 4-bromo-3-butynoyl and        7-chloro-6-heptynoyl.

In R⁷, the C1-C3 alkyl includes, for example, methyl, ethyl and propyl.

In R⁸, the C1-C3 alkyl includes, for example, methyl, ethyl and propyl.

In R⁹ and R¹⁰;

-   -   the halogen atom includes, for example, a fluorine atom and        chlorine atom;    -   the C1-C6 alkyl includes, for example, methyl, ethyl, propyl,        isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,        isopentyl and hexyl;    -   the C1-C6 haloalkyl includes, for example, fluoromethyl,        difluoromethyl, trifluoromethyl, trichloromethyl,        2,2,2-trifluoroethyl, 2,2-difluoroethyl and 2-fluoroethyl;    -   the C2-C6 alkenyl includes, for example, vinyl, 2-propenyl,        1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl,        2-hexenyl and 5-hexenyl;    -   the C2-C6 haloalkenyl includes, for example, 1-chlorovinyl,        2-chlorovinyl, 2,2-dichlorovinyl, 2,2-difluorovinyl,        1,2-dichlorovinyl, 3,3-dichloro-2-propenyl and        3,3-difluoro-2-propenyl;    -   the C2-C6 alkynyl includes, for example, ethynyl, 3-butynyl and        5-hexynyl;    -   the C2-C6 haloalkynyl includes, for example, 2-chloroethynyl,        2-bromoethynyl and 6-chloro-5-hexynyl;    -   the C1-C6 alkoxy, for example, methoxy, ethoxy, propoxy,        isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy,        pentyloxy, isopentyloxy and hexyloxy;    -   the C1-C6 haloalkoxy includes, for example, trifluoromethoxy,        difluoromethoxy, bromodifluoromethoxy, chlorodifluoromethoxy,        fluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy,        5-chloropentyloxy, 4-fluoroisopentyloxy, 2,2-dichlorohexyloxy,        trichloromethoxy, 2,2-difluoroethoxy and 2-fluoroethoxy;    -   the C3-C6 alkenyloxy includes, for example, 2-propenyloxy,        1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy,        3-butenyloxy, 2-hexenyloxy and 5-hexenyloxy;    -   the C3-C6 haloalkenyloxy includes, for example,        3,3-difluoro-2-propenyloxy, 3,3-dichloro-2-propenyloxy,        3,3-dibromo-2-propenyloxy, 2,3-dichloro-2-propenyloxy,        6-fluoro-2-hexenyloxy and 2,2-dichloro-5-hexenyloxy;    -   the C3-C6 alkynyloxy includes, for example, a 2-propynyloxy,        1-methyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 2-hexynyloxy        and 5-hexynyloxy;    -   the C3-C6 haloalkynyloxy includes, for example,        3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy,        3-iodo-2-propynyloxy and 6-chloro-5-hexynyloxy;    -   the cyano C1-C6 alkoxy includes, for example, cyanomethoxy,        1-cyanoethoxy, 2-cyanoethoxy, 2-methyl-2-cyanoethoxy,        1-cyanopropoxy and 2-cyanopropoxy;    -   the C1-C6 alkylthio includes, for example, methylthio,        ethylthio, propylthio, isopropylthio, butylthio, isobutylthio,        sec-butylthio, tert-butylthio, pentylthio, isopentylthio and        hexylthio;    -   the C1-C6 haloalkylthio includes, for example,        trifluoromethylthio, difluoromethylthio,        bromodifluoromethylthio, chlorodifluoromethylthio,        fluoromethylthio, 2,2,2-trifluoroethylthio,        1,1,2,2-tetrafluoroethylthio, 5-chloropentylthio,        4-fluoroisopentylthio and 2,2-dichlorohexylthio;    -   the C3-C6 cycloalkyl includes, for example, cyclopropyl,        cyclobutyl, cyclopentyl and cyclohexyl;    -   the C3-C6 cycloalkoxy includes, for example, cyclopropoxy,        cyclobutoxy, cyclopentoxy and cyclohexyloxy;    -   the tri(C1-C6 alkyl)silyl includes, for example, trimethylsilyl,        triethylsilyl, tributylsilyl and tert-butyldimethylsilyl.

In R¹¹, R¹² and R¹³;

-   -   the halogen atom includes, for example, fluorine atom, chlorine        atom and bromine atom;    -   the C1-C3 alkyl includes, for example, methyl, ethyl and propyl.

The phenyl substituted with R⁹, R¹⁰, R¹¹, R¹² and R¹³ includes, forexample, the phenyl wherein R⁹ and R¹⁰ are C1-C6 alkoxy, and R¹¹, R¹²and R¹³ are a hydrogen atom, halogen atom or C1-C3 alkyl;

-   -   the phenyl wherein R⁹ and R¹⁰ are independently a halogen atom,        C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl,        C2-C6 alkynyl, C2-C6 haloalkynyl, cyano C1-C6 alkyl, C1-C6        alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6        haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, cyano        C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C6        alkenylthio, C3-C6 alkynylthio, C3-C6 cycloalkyl, C3-C6        cycloalkoxy, (C3-C6 cycloalkyl) C1-C3 alkoxy, C2-C6 alkoxyalkyl,        tri(C1-C6 alkyl)silyl or cyano, and R¹¹, R¹² and R¹³ are        hydrogen atoms;    -   the phenyl wherein R⁹ and R¹⁰ are independently C1-C6 alkoxy,        C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6        alkynyloxy, C3-C6 haloalkynyloxy or cyano C1-C6 alkoxy, and R¹¹,        R¹² and R¹³ are hydrogen atoms;    -   the phenyl wherein R⁹ and R¹⁰ are independently C1-C3 alkoxy, C3        alkenyloxy or cyano C1-C3 alkoxy, and R¹¹, R¹² and R¹³ are        hydrogen atoms;    -   the phenyl wherein R⁹ and R¹⁰ are methoxy, and R¹¹, R¹² and R¹³        are hydrogen atoms;    -   the phenyl wherein R⁹ is ethoxy, R¹⁰ is methoxy, and R¹¹, R¹²        and R¹³ are hydrogen atoms;    -   the phenyl wherein R⁹ is 2-propynyloxy, R¹⁰ is methoxy, and R¹¹,        R¹² and R¹³ are hydrogen atoms;    -   the phenyl wherein R⁹ is cyanomethoxy, R¹⁰ is methoxy, and R¹¹,        R¹² and R¹³ are hydrogen atoms.        are put up.

In R¹⁴, R¹⁵, R¹⁶ and R¹⁷;

-   -   the halogen atom includes, for example, a fluorine atom and        chlorine atom;    -   the C1-C6 alkyl includes, for example, methyl, ethyl, propyl,        isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,        isopentyl and hexyl;    -   the C1-C6 haloalkyl includes, for example, fluoromethyl,        difluoromethyl, trifluoromethyl, chlorodifluoromethyl,        chlorofluoromethyl, bromodifluoromethyl, trichloromethyl,        1,1,2,2,2-pentafluoroethyl, 2,2,2-trifluoroethyl,        2,2-difluoroethyl, 2-fluoroethyl and 6,6,6-trifluorohexyl;    -   the C2-C6 alkenyl includes, for example, vinyl, 2-propenyl,        1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl,        2-hexenyl and 5-hexenyl;    -   the C2-C6 haloalkenyl includes, for example, 1-chlorovinyl,        2-chlorovinyl, 2,2-dichlorovinyl, 2,2-difluorovinyl,        1,2-dichlorovinyl, 3,3-difluoro-2-propenyl and        3,3-dichloro-2-propenyl;    -   the C2-C6 alkynyl includes, for example, ethynyl, 3-butynyl and        5-hexynyl;    -   the C2-C6 haloalkynyl includes, for example, 2-chloroethynyl,        2-bromoethynyl and 6-chloro-5-hexynyl;    -   the C1-C6 alkoxy, for example, methoxy, ethoxy, propoxy,        isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy,        pentyloxy, isopentyloxy and hexyloxy;    -   the C1-C6 haloalkoxy includes, for example, trifluoromethoxy,        difluoromethoxy, bromodifluoromethoxy, chlorodifluoromethoxy,        fluoromethoxy, 2,2,2-trifluoroethoxy,    -   1,1,2,2-tetrafluoroethoxy, 5-chloropentyloxy,        4-fluoroisopentyloxy and 2,2-dichlorohexyloxy;    -   the C3-C6 alkenyloxy includes, for example, 2-propenyloxy,        1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy,        3-butenyloxy, 2-hexenyloxy and 5-hexenyloxy;    -   the C3-C6 haloalkenyloxy includes, for example,        3,3-difluoro-2-propenyloxy, 3,3-dichloro-2-propenyloxy,        3,3-dibromo-2-propenyloxy, 2,3-dichloro-2-propenyloxy,        6-fluoro-2-hexenyloxy and 2,2-dichloro-5-hexenyloxy;    -   the C3-C6 alkynyloxy includes, for example, a 2-propynyloxy,        1-methyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 2-hexynyloxy        and 5-hexynyloxy;    -   the C3-C6 haloalkynyloxy includes, for example,        3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy,        3-iodo-2-propynyloxy and 6-chloro-5-hexynyloxy;    -   the C1-C6 alkylthio includes, for example, methylthio,        ethylthio, propylthio, isopropylthio, butylthio, isobutylthio,        sec-butylthio, tert-butylthio, pentylthio, isopentylthio and        hexylthio;    -   the C1-C6 haloalkylthio includes, for example,        trifluoromethylthio, difluoromethylthio,        bromodifluoromethylthio, chlorodifluoromethylthio,        fluoromethylthio, 2,2,2-trifluoroethylthio,        1,1,2,2-tetrafluoroethylthio, 5-chloropentylthio,        4-fluoroisopentylthio and 2,2-dichlorohexylthio;    -   the C3-C6 cycloalkyl includes, for example, cyclopropyl,        cyclobutyl, cyclopentyl and cyclohexyl;    -   the C3-C6 cycloalkoxy includes, for example, cyclopropoxy,        cyclobutoxy, cyclopentoxy and cyclohexyloxy;    -   the tri(C1-C6 alkyl)silyl includes, for example, trimethylsilyl,        triethylsilyl, tributylsilyl and tert-butyldimethylsilyl.

The o-phenylene substituted with R¹⁴, R¹⁵, R¹⁶ and R¹⁷ includes, forexample, the o-phenylene wherein R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independentlya hydrogen atom, halogen atom or C1-C3 alkyl;

-   -   the o-phenylene wherein R¹⁴ is methyl, R¹⁵ is a fluorine atom,        and R¹⁶ and R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ is a chlorine atom, R¹⁶ is a        fluorine atom, and R¹⁵ and R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ is methoxy, R¹⁷ is a chlorine atom,        and R¹⁵ and R¹⁶ are hydrogen atoms;    -   the o-phenylene wherein R¹⁵ is a fluorine atom, R¹⁶ is a        chlorine atom, and R¹⁴ and R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁶ is methoxy, R¹⁷ is methyl, and R¹⁴        and R¹⁵ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁵ are chlorine atoms, and R¹⁶        and R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁶ are chlorine atoms, and R¹⁵        and R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁷ are chlorine atoms, and R¹⁵        and R¹⁶ are hydrogen atoms;    -   the o-phenylene wherein R¹⁵ and R¹⁶ are chlorine atoms, and R¹⁴        and R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁶ and R¹⁷ are chlorine atoms, and R¹⁴        and R¹⁵ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁵ are chlorine atoms, and R¹⁶        and R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁵ are methyl, and R¹⁶ and R¹⁷        are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁶ are methyl, and R¹⁵ and R¹⁷        are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁷ are methyl, and R¹⁵ and R¹⁶        are hydrogen atoms;    -   the o-phenylene wherein R¹⁵ and R¹⁶ are methyl, and R¹⁴ and R¹⁷        are hydrogen atoms;    -   the o-phenylene wherein R¹⁶ and R¹⁷ are methyl, and R¹⁴ and R¹⁵        are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ and R¹⁵ are methyl, and R¹⁶ and R¹⁷        are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ is methyl, and R¹⁵, R¹⁶ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁴ is a chlorine atom, and R¹⁵, R¹⁶ and        R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁴ is methoxy, and R¹⁵, R¹⁶ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁴ is cyano, and R¹⁵, R¹⁶ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁴ is trifluoromethyl, and R¹⁵, R¹⁶ and        R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁵ is methyl, and R¹⁴, R¹⁶ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁵ is chlorine atom, and R¹⁴, R¹⁶ and        R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁵ is methoxy, and R¹⁴, R¹⁶ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁵ is cyano, and R¹⁴, R¹⁶ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁵ is trifluoromethyl, and R¹⁴, R¹⁶ and        R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁶ is methyl, and R¹⁴, R¹⁵ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁶ is a chlorine atom, and R¹⁴, R¹⁵ and        R¹⁷ are hydrogen atoms;    -   the o-phenylene wherein R¹⁶ is methoxy, and R¹⁴, R¹⁵ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁶ is cyano, and R¹⁴, R¹⁵ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁶ is cyano, and R¹⁴, R¹⁵ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁶ is cyclopropyl, R¹⁴, R¹⁵ and R¹⁷ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁷ is methyl, and R¹⁴, R¹⁵ and R¹⁶ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁷ is a chlorine atom, and R¹⁴, R¹⁵ and        R¹⁶ are hydrogen atoms;    -   the o-phenylene wherein R¹⁷ is methoxy, and R¹⁴, R¹⁵ and R¹⁶ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁷ is cyano, R¹⁴, R¹⁵ and R¹⁶ are        hydrogen atoms;    -   the o-phenylene wherein R¹⁷ is methylthio, and R¹⁴, R¹⁵ and R¹⁶        are hydrogen atoms;    -   the o-phenylene wherein R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are hydrogen        atoms.

The embodiments of the present compounds include, for example, thefollowing compounds.

The compound of the formula (1) wherein X¹ is an oxygen atom;

-   -   the compound of the formula (1) wherein X²is an oxygen atom;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms;    -   the compound of the formula (1) wherein R⁷ is a hydrogen atom;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        and R⁷ is a hydrogen atom;    -   the compound of the formula (1) wherein X² is an oxygen atom,        and R⁷ is a hydrogen atom;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, and R⁷ is a hydrogen atom;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        and R⁹ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom,        and R⁹ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, and R⁹ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6        alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁷ is a hydrogen atom,        and R⁹ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom, R⁷        is a hydrogen atom, and R⁹ is C1-C6 alkoxy, C1-C6 haloalkoxy,        C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X²is an oxygen atom, R⁷        is a hydrogen atom, and R⁹ is C1-C6 alkoxy, C1-C6 haloalkoxy,        C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, and R⁹ is C1-C6 alkoxy, C1-C6        haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6        alkynyloxy, C2-C6 haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom,        and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁷is a hydrogen atom,        and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom, R⁷        is a hydrogen atom, and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom, R⁷        is a hydrogen atom, and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        and R¹⁰ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom,        and R¹⁰ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, and R¹⁰ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6        alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁷is a hydrogen atom,        and R¹⁰ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom, R⁷        is a hydrogen atom, and R¹⁰ is C1-C6 alkoxy, C1-C6 haloalkoxy,        C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom, R⁷        is a hydrogen atom, and R¹⁰ is C1-C6 alkoxy, C1-C6 haloalkoxy,        C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, and R¹⁰ is C1-C6 alkoxy, C1-C6        haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6        alkynyloxy, C2-C6 haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom,        and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁷ is a hydrogen atom,        and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom, R⁷        is a hydrogen atom, and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom, R⁷        is a hydrogen atom, and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        and R⁹ and R¹⁰ are independently C1-C6 alkoxy, C1-C6 haloalkoxy,        C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom,        and R⁹ and R¹⁰ are independently C1-C6 alkoxy, C1-C6 haloalkoxy,        C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, and R⁹ and R¹⁰ are independently C1-C6 alkoxy, C1-C6        haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6        alkynyloxy, C2-C6 haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁷ is a hydrogen atom,        and R⁹ and R¹⁰ are independently C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        R⁷is a hydrogen atom, and R⁹ and R¹⁰ are independently C1-C6        alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6        haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or cyano        C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom, R⁷        is a hydrogen atom, and R⁹ and R¹⁰ are independently C1-C6        alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, and R⁹ and R¹⁰ are independently        C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy, C2-C6        haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or cyano        C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom,        and R⁹ and R¹⁰ are independently C1-C6 alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom,        and R⁹ and R¹⁰ are independently C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, and R9 and R¹⁰ are independently C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁷ is a hydrogen atom,        and R⁹ and R¹⁰ are independently C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ is an oxygen atom, R⁷        is a hydrogen atom, and R⁹ and R¹⁰ are independently C1-C6        alkoxy;    -   the compound of the formula (1) wherein X² is an oxygen atom, R⁷        is a hydrogen atom, and R⁹ and R¹⁰ are independently C1-C6        alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷is a hydrogen atom, and R⁹ and R¹⁰ are independently        C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and X¹ is an oxygen atom;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and X² is an oxygen atom;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and X¹ and X2 are oxygen atoms;    -   the compound of the formula (1) wherein R⁴, R⁵ and R⁷ are        hydrogen atoms, and X¹ is an oxygen atom;    -   the compound of the formula (1) wherein R⁴, R⁵ and R⁷ are        hydrogen atoms, and X² is an oxygen atom;    -   the compound of the formula (1) wherein R⁴, R⁵ and R⁷ are        hydrogen atoms, and X¹ and X² are oxygen atoms;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and R⁹ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6        alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and R¹⁰ is C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6        alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and R⁹ and R¹⁰ are C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6        alkenyloxy, C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6        haloalkynyloxy or cyano C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and R⁹ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein R⁴ and R⁵ are hydrogen        atoms, and R⁹ and R¹⁰ are C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, R⁴ and R⁵ are hydrogen atoms, and        R9 is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, R⁴ and R⁵ are hydrogen atoms, and        R¹⁰ is C1-C6 alkoxy;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁷ is a hydrogen atom, R⁴ and R⁵ are hydrogen atoms, and        R⁹ and R¹⁰ are C1-C6 alkoxy;    -   the compound of the formula (1) wherein R¹¹, R¹² and R¹³ are        hydrogen atoms;    -   the compound of the formula (1) wherein R⁴, R⁵, R¹¹, R¹² and R¹³        are hydrogen atoms;    -   the compound of the formula (1) wherein R⁷, R¹¹, R¹² and R¹³ are        hydrogen atoms;    -   the compound of the formula (1) wherein R⁴, R⁵, R⁷, R¹¹, R¹² and        R¹³ are hydrogen atoms;    -   the compound of the formula (1) wherein X¹ and X² is oxygen        atoms, and R⁴, R⁵, R⁷, R¹¹, R¹² and R¹³ are hydrogen atoms;    -   the compound of the formula (1) wherein R¹⁴, R¹⁵, R¹⁶ and R¹⁷        are independently a hydrogen atom, halogen atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein R¹¹, R¹² and R¹³ are        hydrogen atoms, and R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independently a        hydrogen atom, halogen atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein R⁴, R⁵, R¹¹, R¹² and R¹³        is hydrogen atoms, and R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independently a        hydrogen atom, halogen atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein R⁴, R⁵ and R⁷ is        hydrogen atoms, and R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independently a        hydrogen atom, halogen atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein R⁴, R⁵, R⁷, R¹¹, R¹² and        R¹³ is hydrogen atoms, and R¹⁴, R¹⁵, R¹⁶ and R¹⁷ is        independently a hydrogen atom, halogen atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein R¹⁴, R¹⁵, R¹⁶ and R¹⁷        are hydrogen atoms;    -   the compound of the formula (1) wherein R⁴, R⁵, R¹⁴, R¹⁵, R¹⁶        and R¹⁷ are hydrogen atoms;    -   the compound of the formula (1) wherein R¹¹, R¹², R¹³, R¹⁴, R¹⁵,        R¹⁶ and R¹⁷ are hydrogen atoms;    -   the compound of the formula (1) wherein R⁷, R¹⁴, R¹⁵, R¹⁶, and        R¹⁷ are hydrogen atoms;    -   the compound of the formula (1) wherein R⁴, R⁵, R⁷, R¹⁴, R¹⁵,        R¹⁶ and R¹⁷ are hydrogen atoms;    -   the compound of the formula (1) wherein R⁴, R⁵, R¹¹, R¹², R¹³,        R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are hydrogen atoms;    -   the compound of the formula (1) wherein R⁴, R⁵, R⁷, R¹⁴, R¹⁵,        R¹⁶ and R¹⁷ are hydrogen atoms;    -   the compound of the formula (1) wherein R¹⁴, R¹⁵, R¹⁶ and R¹⁷        are independently a hydrogen atom, halogen atom or a C1-C6        alkyl;    -   the compound of the formula (1) wherein R⁹ and R¹⁰ are        independently C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy, R¹¹, R¹² and R¹³ are hydrogen atoms, and        R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independently a hydrogen atom, halogen        atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein R⁹ and R¹⁰ are        independently C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy, R⁴, R⁵, R¹¹, R¹² and R¹³ are hydrogen atoms,        and R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independently a hydrogen atom,        halogen atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein R⁹ and R¹⁰ are        independently C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy, R⁴, R⁵ and R⁷ are hydrogen atoms, and R¹⁴,        R¹⁵, R¹⁶ and R¹⁷ are independently a hydrogen atom, halogen atom        or C1-C6 alkyl;    -   the compound of the formula (1) wherein R⁹ and R¹⁰ are        independently C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyloxy,        C2-C6 haloalkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkynyloxy or        cyano C1-C6 alkoxy, R⁴, R⁵, R⁷, R¹¹, R¹² and R¹³ are hydrogen        atoms, and R¹⁴, R¹⁵, R¹⁶ and R¹⁷ are independently a hydrogen        atom, halogen atom or C1-C6 alkyl;    -   the compound of the formula (1) wherein X¹ and X² are oxygen        atoms, R⁹ and R¹⁰ are independently C1-C6 alkoxy, C1-C6        haloalkoxy, C2-C6 alkenyloxy, C2-C6 haloalkenyloxy, C2-C6        alkynyloxy, C2-C6 haloalkynyloxy or cyano C1-C6 alkoxy, R⁴, R⁵,        R⁷, R¹¹, R¹² and R¹³ are hydrogen atoms, and R¹⁴, R¹⁵, R¹⁶ and        R¹⁷ are independently a hydrogen atom, halogen atom or C1-C6        alkyl.

The following describes a production process for the present compound.

The present compound can be produced by, for example, (ProductionProcess A), (Production Process B), (Production Process C) or(Production Process D).

(Production Process A)

The present compound of the formula (4) can be produced by making thecompound of the formula (2) react with the compound of the formula (3).

wherein L¹ represents a chlorine atom, bromine atom ormethanesulfonyloxy, and R¹ to R¹⁷ have the same meaning as describedabove.

The reaction is carried out in the presence or absence of a solvent, andusually in the presence of base.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; halogenated hydrocarbons such as chlorobenzene andthe like; esters such as ethyl acetate, butyl acetate and the like;nitriles such as acetonitrile, butyronitrile and the like; acid amidessuch as N,N-dimethylformamide and the like; sulfoxides such asdimethylsulfoxide and the like; and the mixture thereof.

The base used in the reaction includes, for example, carbonates such assodium carbonate, potassium carbonate and the like; alkali metalhydrides such as sodium hydride and the like; tertiary amines such astriethylamine, diisopropylethamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; nitrogen containingaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

Concerning the ratio of the compound used in the reaction, the amount ofthe compound of the formula (3) is usually 1 to 10 mole, and the amountof the base is usually 1 to 10 mole, based on 1 mole of the compound ofthe formula (2).

The reaction time is usually in the range of 0.1 to 24 hours, and thereaction temperature is usually in the range of 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (4). Even more, the isolated presentcompound of the formula (4) can be purified by a technique such aschromatography, recrystallization and the like.

(Production Process B)

The present compound of the formula (6) can be produced by making thecompound of the formula (5) react with

-   -   2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide        (Lawesson's reagent; hereinafter referred to as Lawesson's        reagent).        wherein R¹ to R¹⁷ and X² have the same meaning as described        above.

The reaction is usually carried out in solvents. The solvent used in thereaction includes, for example, ethers such as 1,4-dioxane,tetrahydrofuran, ethylene glycol dimethyl ether, tert-butyl methyl etherand the like; aliphatic hydrocarbons such as hexane, heptane, octane andthe like; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; nitritessuch as acetonitrile, butyronitrile and the like; sulfoxides such asdimethylsulfoxide and the like; and the mixture thereof.

The amount of Lawesson's reagent is usually 1 to 10 mole based on 1 moleof the compound of the formula (5).

The reaction time is usually in the range of 0.5 to 24 hours, and thereaction temperature is usually in the range of 50 to 150° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (6). Even more, the isolated presentcompound of the formula (6) can be purified by a technique such aschromatography, recrystallization and the like.

(Production Process C)

The present compound of the formula (9) can be produced by making thecompound of the formula (7) react with the compound of the formula (8).

wherein L² represents a bromine atom, iodine atom or methanesulfonyloxy,R^(8a) represents C1-C3 alkyl, R¹ to R⁷, R⁹ to R¹⁷, X¹ and X² have thesame meaning as described above.

The reaction is carried out in the presence or absence of a solvent, andusually in the presence of base.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; halogenated hydrocarbons such as chlorobenzene andthe like; esters such as ethyl acetate, butyl acetate and the like;nitriles such as acetonitrile, butyronitrile and the like; acid amidessuch as N,N-dimethylformamide and the like; sulfoxides such asdimethylsulfoxide and the like; and the mixture thereof.

The base used in the reaction includes, for example, carbonates such assodium carbonate, potassium carbonate and the like; alkali metalhydrides such as sodium hydride and the like.

Concerning the ratio of the compound used in the reaction, the amount ofthe compound of the formula (8) is usually 1 to 10 mole, and the amountof the base is usually 1 to 10 mole, based on 1 mole of the compound ofthe formula (7).

The reaction time is usually in the range of 0.5 to 24 hours, and thereaction temperature is usually in the range of 0 to 120° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (9). Even more, the isolated presentcompound of the formula (9) can be purified by a technique such aschromatography, recrystallization and the like.

(Production Process D)

The present compound of the formula (13) can be produced by making thecompound of the formula (10) react with methanesulfonyl chloride, andsubsequently making react with the compound of the formula (12).

wherein R¹ to R⁷, R⁹ to R¹² and X² have the same meaning as describedabove.[Step 1]: The Process of Making the Compound of the Formula (10) Reactwith Methanesulfonyl Chloride.

The reaction is carried out usually in a solvent, and usually in thepresence of base.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; halogenated hydrocarbons such as chlorobenzene andthe like; esters such as ethyl acetate, butyl acetate and the like;nitriles such as acetonitrile, butyronitrile and the like; acid amidessuch as N,N-dimethylformamide and the like; sulfoxides such asdimethylsulfoxide and the like; and the mixture thereof.

The base used in the reaction includes, for example, carbonates such assodium carbonate, potassium carbonate and the like; alkali metalhydrides such as sodium hydride and the like; tertiary amines such astriethylamine, diisopropylethamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; nitrogen containingaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

Concerning the ratio of the compound used in the reaction, the amount ofthe base is usually 1 to 10 mole, and the amount of methanesulfonylchloride is usually 1 to 3 mole, based on 1 mole of the compound of theformula (10).

The reaction time is usually in the range of 1 to 24 hours, and thereaction temperature is usually in the range of −20 to 100° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (11). Even more, the isolated presentcompound of the formula (11) can be purified by a technique such aschromatography, recrystallization and the like.

[Step 2]: The Process of Making the Compound of the Formula (11) Reactwith the Compound of the Formula (12).

The reaction is carried out in the presence or absence of a solvent, andin the presence or absence of base.

The solvent used in the reaction, if required, includes, for example,ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethylether, tert-butyl methyl ether and the like; aliphatic hydrocarbons suchas hexane, heptane, octane and the like; aromatic hydrocarbons such astoluene, xylene and the like; halogenated hydrocarbons such aschlorobenzene and the like; esters such as ethyl acetate, butyl acetateand the like; nitrites such as acetonitrile, butyronitrile and the like;acid amides such as N,N-dimethylformamide and the like; sulfoxides suchas dimethylsulfoxide and the like; and the mixture thereof.

The base used in the reaction, if required, includes, for example,carbonates such as sodium carbonate, potassium carbonate and the like;tertiary amines such as triethylamine, diisopropylethamine,1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene andthe like; nitrogen containing aromatic compounds such as pyridine,4-dimethylaminopyridine and the like.

The amount of the compound of the formula (12) is usually 1 to 10 molebased on 1 mole of the compound of the formula (11).

The reaction time is usually in the range of 1 to 24 hours, and thereaction temperature is usually in the range of 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (13). Even more, the isolated presentcompound of the formula (13) can be purified by a technique such aschromatography, recrystallization and the like.

The following describes a production process for the intermediatecompound of the present compound.

The compound of the formula (19) can be produced by, for example, thefollowing scheme.

wherein L³ represents a chlorine atom or bromine atom, L⁴ represents achlorine atom, bromine atom, iodine atom or trifluoromethanesulfonyloxy,L⁵ represents B(OH)₂, B(OR¹⁹)₂ or SnR²⁰, R¹⁹ and R²⁰ represent C1-C10alkyl, and R¹ to R⁵, R⁷ and R⁹ to R¹⁷ have the same meaning as thedescribed above.[Step5-1]

The compound of the formula (16) can be produced by making the compoundof the formula (14) react with the compound of the formula (15).

The reaction is carried out usually in solvents, and usually in thepresence of base.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; halogenated hydrocarbons such as chlorobenzene andthe like; esters such as ethyl acetate, butyl acetate and the like;nitriles such as acetonitrile, butyronitrile and the like; acid amidessuch as N,N-dimethylformamide; sulfoxides such as dimethylsulfoxide andthe like; and the mixture thereof.

The base used in the reaction includes, for example, carbonates such assodium carbonate, potassium carbonate and the like; tertiary amines suchas triethylamine, diisopropylethamine,1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene andthe like; nitrogen containing aromatic compounds such as pyridine,4-dimethylaminopyridine and the like.

Concerning the ratio of the compound used in the reaction, the amount ofthe base is usually 1 to 10 mole, and the amount of the compound of theformula (15) is usually 1 to 3 mole, based on 1 mole of the compound ofthe formula (14).

The reaction time is usually in the range of 1 to 24 hours, and thereaction temperature is usually in the range of −20 to 100° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (16). Even more, the isolated presentcompound of the formula (16) can be purified by a technique such aschromatography, recrystallization and the like.

[Step5-2]

The compound of the formula (17) wherein R⁷ is a hydrogen atom can beproduced by making the compound of the formula (16) react with areducing agent.

The reaction is carried out usually in solvents.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; water; and the mixture thereof.

The reducing agent used in the reaction includes, for example, sodiumborohydride and potassium borohydride.

The amount of the reducing agent is usually 0.25 to 3 mole based on 1mole of the compound of the formula (16).

The reaction time is usually in the range of instant to 24 hours, andthe reaction temperature is usually in the range of −20 to 100° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (17). Even more, the isolated presentcompound of the formula (17) can be purified by a technique such aschromatography, recrystallization and the like.

The compound of the formula (17) wherein R⁷ is C1-C3 alkyl can beproduced by making the compound of the formula (16) react with anorganic metal compound such as Grignard reagent, alkyl lithium and thelike.

The reaction is carried out usually in solvents.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like.

The amount of the organic metal compound is usually 1 to 3 mole based on1 mole of the compound of the formula (16).

The reaction time is usually in the range of instant to 24 hours, andthe reaction temperature is usually in the range of −80 to 50° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (17). Even more, the isolated presentcompound of the formula (17) can be purified by a technique such aschromatography, recrystallization and the like.

[Step5-3]

The compound of the formula (19) can be produced by making the compoundof the formula (17) react with the compound of the formula (18) in thepresence of a catalyst.

The reaction is carried out usually in a solvent, and usually in thepresence of base.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; halogenated hydrocarbons such as chlorobenzene andthe like; nitrites such as acetonitrile, butyronitrile and the like;acid amides such as N,N-dimethylformamide; sulfoxides such asdimethylsulfoxide and the like; and the mixture thereof.

The catalyst used in the reaction includes, for example, palladiumcompounds such as palladium acetate, tetrakis(triphenylphosphine)palladium, {1,1-bis(diphenylphosphino)ferrocene}palladium dichloridemethylene chloride complex, bis(triphenylphosphine)palladium dichlorideand the like.

Concerning the ratio of the compound used in the reaction, the amount ofthe compound of the formula (17) is usually 1 to 5 mole, and the amountof the catalyst is usually 0.001 to 0.1 mole, based on 1 mole of thecompound of the formula (18).

As the need arises, the reaction may be carried out in the presence of abase (for example, an inorganic base such as sodium acetate, potassiumacetate, potassium phosphate, sodium hydrogencarbonate and the like)and/or phase transfer catalyst (for example, tertiary ammonium salt suchas tetrafluorobenzyl bromide, benzyl triethylammonium bromide and thelike).

The reaction time is usually in the range of 0.2 to 24 hours, and thereaction temperature is usually in the range of 50 to 120° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (19). Even more, the isolated presentcompound of the formula (19) can be purified by a technique such aschromatography, recrystallization and the like.

The compound of the formula (14) can be produced by, for example, thefollowing scheme.

wherein R¹ to R⁵ and L³ have the same meaning as the described above.[Step 6-1]

The compound of the formula (22) can be produced by making the compoundof the formula (21) react with a cyanide compound.

The reaction is carried out usually in solvents.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; nitriles such as acetonitrile, butyronitrile andthe like; acid amides such as N,N-dimethylformamide; sulfoxides such asdimethylsulfoxide and the like; and the mixture thereof.

The cyanide compound used in the reaction includes, for example, alkalimetal cyanide such as sodium cyanide, potassium cyanide and the like;and cupric cyanide.

The amount of the cyanide compound is usually 1 to 5 mole based on 1mole of the compound of the formula (21).

The reaction time is usually in the range of 1 to 24 hours, and thereaction temperature is usually in the range of 50 to 100° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (22). Even more, the isolated presentcompound of the formula (22) can be purified by a technique such aschromatography, recrystallization and the like.

[Step 6-2]

The compound of the formula (23) can be produced by making the compoundof the formula (22) hydrolyze under acidic condition.

The reaction is carried out usually in the presence of an acid andwater, and, if necessary, in a organic solvents.

The acid used in the reaction includes, for example, hydrochloric acid,hydrobromic acid and sulfuric acid.

The amount of the acid is usually 1 mole to excess amount based on 1mole of the compound of the formula (22).

The reaction time is usually in the range of 1 to 40 hours, and thereaction temperature is usually in the range of 40 to 100° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (23). Even more, the isolated presentcompound of the formula (23) can be purified by a technique such aschromatography, recrystallization and the like.

[Step 6-3]

The compound of the formula (14) can be produced by making the compoundof the formula (23) react with a chlorinating agent or brominatingagent.

The reaction is carried out usually in the presence or absence of asolvent.

The solvent used in the reaction includes, for example, ethers such as1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, tert-butylmethyl ether and the like; aliphatic hydrocarbons such as hexane,heptane, octane and the like; aromatic hydrocarbons such as toluene,xylene and the like; halogenated hydrocarbons such as chlorobenzene andthe like; nitriles such as acetonitrile, butyronitrile and the like; andthe mixture thereof.

The chlorinating agent and brominating agent used in the reactionincludes, for example, thionyl chloride, phosphorous oxychloride,phosphorous chloride and thionyl bromide.

The amount of the chlorinating agent or brominating agent used in thereaction is usually 1 to 5 mole based on 1 mole of the compound of theformula (23).

The reaction time is usually in the range of 0.1 to 24 hours, and thereaction temperature is usually in the range of 50 to 150° C.

After completion of the reaction, the reaction mixture is subjected tousual post treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thepresent compound of the formula (14). Even more, the isolated presentcompound of the formula (14) can be purified by a technique such aschromatography, recrystallization and the like.

Examples of the plant diseases to be controlled by the present compoundinclude, for example,

-   -   Pyricularia oryzae and Cochliobolus miyabeanus and Rhizoctonia        solani of rice; Erysiphe graminis, Gibberella zeae, Puccinia        striiformis, P. graminis, P. recondita, P. hordei, Typhula sp.,        Micronectriella nivalis, Ustilago tritici, U. nuda, Tilletia        caries, Pseudocercosporella herpotrichoides, Rhynchosporium        secalis, Septoria tritici and Leptosphaeria nodorum, of wheat        and barley; Diaporthe citri, Elsinoe fawcetti, Penicillium        digitatum and P. italicum of citrus; Sclerotinia mali, Valsa        mali, Podosphaera leucotricha, Alternaria mali and Venturia        inaequalis of apple; Venturia nashicola, V. pirina, Alternaria        kikuchiana and Gymnosporangium haraeanum of pear; Sclerotinia        cinerea, Cladosporium carpophilum and Phomopsis sp. of peach;        Elsinoe ampelina, Glomerella cingulata, Uncinula necator,        Phakopsora ampelopsidis, Guignardia bidwellii and Plasmopara        viticola, of grape; Gloeosporium kaki, Cercospora kaki and        Mycosphaerella nawae of Japanese persimmon; Colletotrichum        lagenarium, Sphaerothecafuliginea, Mycosphaerella melonis,        Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp.        and Pythium sp. of gourd; Alternaria solani, Cladosporium fulvum        and Phytophthora infestans of tomato; Phomopsis vexans and        Erysiphe cichoracearum, of eggplant; Alternaria japonica and        Cercosporella brassicae of Cruciferae vegetables; Puccinia allii        of leek; Cercospora kikuchii, Elsinoe glycines and        Diaporthephaseolorum var. sojae of soybean; Colletotrichum        lindemthianum of kidney bean; Cercospora personata and        Cercospora arachidicola of peanut; Erysiphe pisi of pea;        Alternaria solani and Phytophthora infestans of potato;        Sphaerotheca humuli of strawberry; Exobasidium reticulatum and        Elsinoe leucospila of tea; Alternaria longipes, Erysiphe        cichoracearum, Colletotrichum tabacum, Peronospora tabacina and        Phytophthora nicotianae of tobacco; Cercospora beticola of sugar        beet; Diplocarpon rosae and Sphaerotheca pannosa of rose;        Septoria chrysanthemi-indici and Puccinia horiana of        chrysanthemum; and Botrytis cinerea and Sclerotinia sclerotiorum        of various crops.

When the present compound is used for controlling plant diseases byapplying the present compound, it can be used as the present compounditself, but usually as a fungicidal composition containing the presentcompound and an appropriate carrier. The fungicidal composition of thepresent invention is usually formulated to emulsifiable concentrates,wettable powders, water dispersible granules, flowables, dusts, granulesand so on by mixing with solid carrier, liquid carrier, surfactant orthe other auxiliaries. These formulations usually contain 0.1 to 90% byweight of the present compound.

Examples of the solid carrier utilized for the formulation include finepowders or granules of minerals such as kaolin clay, attapulgite clay,bentonite, montmorillonite, terra alba, pyrophyllite, talc, diatomaceousearth and calcite; natural organic substances such as corncob and walnutshell; synthetic organic substances such as urea; salts such as calciumcarbonate and ammonium sulfate; and synthetic inorganic substances suchas synthetic hydrous silicon oxide. Examples of the liquid carrierinclude aromatic hydrocarbons such as xylene, alkylbenzene andmethylnaphthalene; alcohols such as isopropanol, ethylene glycol,propylene glycol and cellosolve; ketones such as acetone, cyclohexanoneand isophorone; vegetable oils such as soybean oil and cottonseed oil;paraffin type aliphatic hydrocarbons; esters; dimethyl sulfoxide;acetonitrile and water.

Examples of the surfactant include anionic surfactants such asalkylsulfate ester salts, alkylarylsulfonate salts, dialkylsulfosaccinate salts, polyoxyethylenealkylary ether phosphate salts,ligninsulfonate salts and naphthalenesulfonate formaldehyde condensate;nonionic surfactants such as polyoxyethylenealkylary ether,polyoxyethylenealkylpolyoxypropylene block copolymers and sorbitan fattyacid esters.

Examples of the auxiliaries for formulation include water solublepolymers such as polyvinyl alcohol and polyvinylpyrrolidone;polysaccharides such as gum arabic, alginic acid and its salts, CMC(carboxymethylcellulose) and xanthan gum; inorganic substances such asaluminium magnesium silicate and alumina sol; preservatives; coloringagent; PAP (isopropyl acid phosphate) and stabilizers such as BHT.

By applying the fungicidal composition of the present invention to aplant, the plant can be protected from plant diseases, namely the plantdiseases can be controlled. By applying the fungicidal composition ofthe present invention to a soil, the plant growing on the soil can beprotected from plant diseases, namely the plant diseases can becontrolled.

When the plant disease controlling composition of the present inventionis used with foliar application to a plant or soil application, theapplication amount, although it may vary with a kind of crops, a kind ofplant disease to be controlled, an extent of breaking out plant diseaseto be controlled, formulation types, the time of application, theweather conditions and the like, is usually in the range of 1 to 5,000g, preferably 5 to 1,000 g, 10,000 m².

The emulsifiable concentrates, wettable powders, flowables and the likeare usually applied by spraying after diluted with water. In this case,the concentrate of the present compound is usually in the range of0.0001 to 3 weight %, preferably 0.0005 to 1 weight %. The dusts,granules and the like are usually applied as such without any dilution.

The present fungicidal composition of the present invention can be usedwith the other application such as seed treatment. The method includes,for example, soaking seeds in the fungicidal composition of the presentinvention of 1 to 1000 ppm, spraying or daubing the fungicidalcomposition of the present invention of 1 to 1000 ppm on seeds, andpowder coating seeds with the fungicidal composition of the presentinvention.

The method for controlling plant diseases of the present invention isusually carried out by applying an effective amount of the presentcompound on the plant wherein occurrence of a plant disease ispredictable, and/or the soil wherein the plant is growing.

The fungicidal composition of the present invention can be used asagricultural/horticultural plant diseases controlling composition,namely plant diseases controlling composition in the plowed fields,paddy fields, orchards, tea plantations, pastures, lawns and the like.

Also, the fungicidal composition of the present invention can be usedwith other plant diseases controlling composition, insecticides,acaricides, nematocides, herbicides, plant growth regulators and/orfertilizers.

Examples of such other plant diseases controlling composition include:chlorothalonil; fluazinam; dichlofluanid; fosetyl-Al; cyclic imidederivatives such as captan, captafol, folpet and the like;dithiocarbamate derivatives such as maneb, mancozeb, thiuram, ziram,zineb, propineb and the like; inorganic or organic copper derivativessuch as basic copper sulfate, basic copper chloride, copper hydroxide,copper-oxinate and the like; acylalanine derivatives such as metalaxyl,furalaxyl, ofurace, cyprofuram, benalaxyl, oxadixyl and the like;strobilurine compound such as kresoxim-methyl, azoxystrobin,trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin and thelike; anilinopyrimidine derivatives such as cyprodinil, pyrimethanil,mepanipyrim and the like; phenyl pyrrole derivatives such asfenpiclonil, fludioxonil and the like; imide derivatives such asprocymidone, iprodione, vinclozolin and the like; benzimidazolederivatives such as carbendazim, benomyl, thiabendazole, thiophanatemethyl and the like; amine derivatives such as fenpropimorph,tridemorph, fenpropidin, spiroxamine and the like; azole derivativessuch as propiconazole, triadimenol, prochloraz, penconazole,tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole,difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole,myclobutanil, fenbuconazole, hexaconazole, fluquinconazole,triticonazole, bitertanol, imazalil, flutriafol and the like; cymoxanil;dimethomorph; famoxyadone, fenamidone; iprovalicarb; benthiavalicarb;cyazofamid, zoxamide, ethaboxam; nicobifen; fenhexamid; quinoxyfen;diethofencarb and acibenzolar S-methyl.

The following production examples, formulation examples and testexamples and the like describe the invention further in detail below,but do not limit the scope of the invention.

At first the production examples of the present compound is shown. Inaddition, a number of the present compound is a compound number asdescribed in the following tables.

PRODUCTION EXAMPLE 1

In 10 ml of diethyl ether were added 3.64 g ofN-3′,4′-dimethoxybiphenyl-2-yl)-2-hydroxy-2-(4-methylphenyl)acetamideand 0.30 ml of triethylamine, and 0.15 ml of methanesulfonyl chloridewas added dropwise at about 0° C. The mixture was stirred at roomtemperature for 1 hour. After the addition of water, the reactionmixture was extracted with ethyl acetate. The organic layer was washedtwo times with water, dried over anhydrous magnesium sulfate, andconcentrated under reduced pressure. The obtained residue and 2 ml of2-propyN-1-ol were mixed, and stirred at about 80° C. for 30 minutes.The reaction mixture was cooled to room temperature, and extracted withethyl acetate after the addition of water. The organic layer wassuccessively washed with water, a saturated sodium bicarbonate aqueoussolution, and a saturated sodium chloride aqueous solution; dried overanhydrous magnesium sulfate, and concentrated under reduced pressure.The residue was subjected to silica gel column chromatography to obtain311 mg ofN-3′,4′-dimethoxybiphenyl-2-yl)-2-(propynyloxy)-2-(4-methylphenyl)acetamide(the present compound 1-063).

¹H-NMR (CDCl₃, TMS) d (ppm): 8.79 (1H, s), 8.38 (1H, d, J=8.4 Hz),7.13-7.35 (7H, m), 7.01 (1H, d, J=8.0 Hz), 6.95 (1H, dd, J=8.4, 2.0 Hz),6.90 (1H, d, J=2.0 Hz), 5.01 (1H, s), 3.88-4.05 (8H, m), 2.44 (1H, t,J=2.4 Hz), 2.33 (3H, s)

PRODUCTION EXAMPLE 2

From2-(4-ethylphenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand propargyl alcohol,N-(3′,4′-dimethoxybiphenyl-2-yl)-2-(4-ethylphenyl)-2-(2-propynyloxy)acetamide(the present compound 1-064) was obtained by the similar method ofProduction Example 1.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.80 (1H, br), 8.38 (1H, dd, J=1.2, 8.3Hz), 7.1-7.4 (7H, m), 7.00 (1H, d, J=8.0 Hz), 6.96 (1H, dd, J=2.0, 8.0Hz), 6.91 (1H, d, J=2.0 Hz), 5.01 (1H, s), 4.07 (1H, dd, J=2.4, 15.8Hz), 3.96 (3H, s), 3.90 (1H, dd, J=2.4, 15.6 Hz), 3.90 (3H, s), 2.63(2H, q, J=7.7, 15.2 Hz), 2.44 (1H, t, J=2.4 Hz), 1.21 (3H, t, J=7.7 Hz)

PRODUCTION EXAMPLE 3

From2-(4-methoxyphenyl)-N-(3′,4′-dimethoxybiphenyl-2-yl)-2-hydroxyacetamideand propargyl alcohol,N-(3′,4′-dimethoxybiphenyl-2-yl)-2-(4-methoxyphenyl)-2-(2-propynyloxy)acetamide(the present compound 1-080) was obtained by the similar method ofProduction Example 1.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.78 (1H, br), 8.38 (1H, d, J=8.7 Hz),7.2-7.4 (4H, m), 7.1-7.2 (1H, m), 6.8-7.0 (5H, m), 4.99 (1H, s), 4.0-4.1(1H, m), 3.95 (3H, s), 3.90 (3H, s), 3.8-3.9 (1H, m), 3.79 (3H, s), 2.44(1H, t, J=2.4 Hz)

PRODUCTION EXAMPLE 4

From2-(4-methylphenyl)-N-(3′,4′-dimethoxy-4-methylbiphenyl-2-yl)-2-hydroxyacetamideand propargyl alcohol,N-(3′,4′-dimethoxy-4-methylbiphenyl-2-yl)-2-(2-propynyloxy)-2-(4-methylphenyl)acetamide(the present compound 2-078) was obtained by the similar 10 method ofProduction Example 1.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.75 (1H, br), 8.23 (1H, s), 7.1-7.3 (5H,m), 6.8-7.0 (4H, m), 5.00 (1H, s), 4.06 (1H, dd, J=2.4, 15.8 Hz), 3.94(3H, s), 3.90 (1H, dd, J=2.2, 15.6 Hz), 3.89 (3H, s), 2.44 (1H, t, J=2.4Hz), 2.35 (3H, s), 2.32 (3H, s)

PRODUCTION EXAMPLE 5

From2-(3-methylphenyl)-n-(3′,4′-dimethoxybiphenyl-2-yl)-2-hydroxyacetamideand propargyl alcohol,N-(3′,4′-dimethoxybiphenyl-2-yl)-2-(2-propynyloxy)-2-(3-methylphenyl)acetamide(the present compound 1-098) was obtained by the similar method ofProduction Example 1.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.80 (1H, br), 8.28 (1H, d, J=8.3 Hz),7.1-7.4 (5H, m), 7.00 (1H, d, J=8.3 Hz), 6.95 (1H, dd, J=1.9, 8.2 Hz),6.91 (1H, d, J=1.9 Hz), 5.00 (1H, s), 4.08 (1H, dd, J=2.4, 15.6 Hz),3.95 (3H, s), 3.90 (1H, dd, J=2.4, 15.7 Hz), 3.90 (3H, s), 2.4-2.5 (1H,m)

PRODUCTION EXAMPLE 6

In 6 ml of N,N-dimethylformamide were added 0.47 g ofN-(3′-methoxy-4′-hydroxybiphenyl-2-yl)-2-hyrdoxy-2-(4-methylphenyl)acetamide,0.30 g of 3-bromo-1-propyn and 0.92 g of cesium carbonate, and thereaction mixture was stirred at 0 to 5° C. for 1 hour, at roomtemperature for 1 hour, furthermore at 60° C. for 3 hour. The reactionmixture was cooled to room temperature, and extracted with ethyl acetateafter addition of water. The organic layer was washed with 5%hydrochloric acid, and saturated sodium chloride aqueous solutionsuccessively, dried over anhydrous magnesium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to obtain 225 mg of N-(3′-methoxy-4′-(2-propynyloxy)biphenyl-2-yl)-2-(2-propynyloxy)-2-(4-methylphenyl)acetamide(the present compound 2-025).

¹H-NMR (CDCl₃, TMS) d (ppm): 8.78 (1H, s), 8.38 (1H, d, J=8.1 Hz),7.13-7.35 (8H, m), 6.92-6.94 (2H, m), 5.01 (1H, s), 3.88-4.10 (5H, m),2.55-2.56 (1H, m), 2.45-2.46 (1H, m), 2.33 (3H, s)

PRODUCTION EXAMPLE 7

In 15 ml of ethylene glycol dimethyl ether were added 1.20 g of N-(3′,4′-dimethoxy-6-methylbiphenyl-2-yl)-2-hyrdoxy-2-(4-methylphenyl)acetamide,1.22ml of 30% sodium hydroxide aqueous solution, 50 mg oftetrabutylammonium bromide and 543 mg 3-bromopropyne/5 ml of toluenesolution at room temperature, the mixture was stirred at 40° C. for 6hours. The reaction mixture was cooled to room temperature, and 10extracted with ethyl acetate after addition of water. The organic layerwas washed with saturated sodium chloride aqueous solution, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure.The residue was subjected to silica gel column chromatography to obtain833 mg ofN-(3′,4′-dimethoxy-6-methylbiphenyl-2-yl)-2-(2-propynyloxy)-2-(4-methylphenyl)acetamide(the present compound 2-046).

¹H-NMR (CDCl₃, TMS) d (ppm): 8.39 and 8.34 (1H in all, br), 8.1-8.3 (1H,m), 7.0-7.3 (7H, m), 6.6-6.9 (2H, m), 4.89 and 4.88 (1H in all, s),3.8-4.0 (8H, m), 2.4-2.5 (1H, m), 2.32 and 2.31 (3H in all, s), 2.08(3H, s)

PRODUCTION EXAMPLE 8

In 5 ml of N,N-dimethylformamide were added 500 mg ofN-(3′,4′-dimethoxy-5-methyl-biphenyl-2-yl)-2-hyrdoxy-2-(4-methylphenyl)acetamide,667 mg of cesium carbonate and 226 mg of 3-bromopropyne, the mixture wasstirred at 60° C. for 3.5 hours. The reaction mixture was cooled to roomtemperature, and extracted with ethyl acetate after addition of water.The organic layer was washed with saturated sodium chloride aqueoussolution, dried over anhydrous magnesium sulfate, and concentrated underreduced pressure. The residue was subjected to silica gel columnchromatography to obtain 130 mg ofN-(3′,4′-dimethoxy-5-methyl-biphenyl-2-yl)-2-(2-propynyloxy)-2-(4-methylphenyl)acetamide(the present compound 2-062).

¹H-NMR (CDCl₃, TMS) d (ppm): 8.68 (1H, br), 8.22 (1H, d, J=8.3 Hz),7.0-7.3 (6H, m), 6.98 (1H, d, J=8.3 Hz), 6.93 (1H, dd, J=1.8, 8.2 Hz),6.88 (1H, d, J=1.9 Hz), 4.99 (1H, s), 4.06 (1H, dd, J=2.4, 15.8 Hz),3.95 (3H, s), 3.89 (1H, dd, J=2.4, 15.6 Hz), 3.89 (3H, s), 2.43 (1H, t,J=2.2 Hz), 2.33 (3H, s), 2.32 (3H, s)

PRODUCTION EXAMPLE 9

In 10 ml of tetrahydrofuran were added 0.70 g of2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand 231 mg of triethylamine, and 241 mg of methanesulfonyl chloride wasadded dropwise at about 0° C. The mixture was stirred at the sametemperature for 30 minutes and at room temperature for 60 minutes. Afteraddition of water, the reaction mixture was extracted with ethylacetate. The organic layer was washed with 5% hydrochloric acid andsaturated sodium chloride aqueous solution, dried over anhydrousmagnesium sulfate, and concentrated under reduced pressure to obtain3.43 g of a residue. 0.69 g of the obtained residue and 0.81 g2-propyn-1-ol were mixed, and stirred at about 80° C. for 2 hours. Thereaction mixture was cooled to room temperature, and extracted withethyl acetate after addition of water. The organic layer was washed withsaturated sodium chloride aqueous solution, dried over anhydrousmagnesium sulfate, and concentrated under reduced pressure. The residuewas subjected to silica gel column chromatography to obtain 180 mg of2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-(2-propynyloxy)acetamide(the present compound 1-060).

¹H-NMR (CDCl₃, TMS) d (ppm): 8.74 (1H, br), 8.33 (1H, d, J=8.4 Hz),7.2-7.4 (6H, m), 7.1-7.2 (1H, m), 6.8-7.1 (3H, m), 5.02 (1H, s), 3.9-4.2(2H, m), 3.96 (3H, s), 3.89 (3H, s), 2.46 (1H, t, J=2.3 Hz)

PRODUCTION EXAMPLE 10

From 2-phenyl-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamide andpropargyl alcohol,N-(3′,4′-dimethoxybiphenyl-2-yl)-2-phenyl-2-(2-propynyloxy)acetamide(the present compound 1-058) was obtained by the similar method ofProduction Example 9.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.77 (1H, br), 8.37 (1H, dd, J=0.97, 8.3Hz), 7.2-7.5 (7H, m), 7.1-7.2 (1H, m), 7.00 (1H, d, J=8.0 Hz), 6.94 (1H,dd, J=2.0, 8.3 Hz), 6.90 (1H, d, J=2.0 Hz), 5.03 (1H, s), 3.8-4.2 (2H,m), 3.96 (3H, s), 3.89 (3H, s), 2.45 (1H, J=2.4 Hz)

PRODUCTION EXAMPLE 11

From2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand methanol,2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-methoxyacetamide(the present compound 1-003) was obtained by the similar method ofProduction Example 9.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.72 (1H, br), 8.31 (1H, d, J=8.0 Hz),7.1-7.4 (7H, m), 6.98 (1H, d, J=7.8 Hz), 6.90 (1H, dd, J=2.0, 8.0 Hz),6.87 (1H, d, J=1.9 Hz), 4.61 (1H, s), 3.97 (3H, s), 3.88 (3H, s), 3.25(3H, s)

PRODUCTION EXAMPLE 12

From2-(4-fluorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand propargyl alcohol2-(4-fluorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-(2-propynyloxy)acetamide(the present compound 1-059) was obtained by the similar method ofProduction Example 9.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.77 (1H, br), 8.30 (1H, dd, J=8.3, 0.97Hz), 7.2-7.4 (4H, m), 7.1-7.2 (1H, m), 7.0-7.1 (3H, m), 6.93 (1H, dd,J=1.9, 8.3 Hz), 6.89 (1H, d, J=1.9 Hz), 5.02 (1H, s), 4.08 (1H, dd,J=2.4, 15.6 Hz), 3.95 (3H, s), 3.91 (1H, dd, J=2.4, 15.6 Hz), 3.89 (3H,s), 2.46 (1H, t, J=2.4 Hz)

PRODUCTION EXAMPLE 13

From2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideethyl alcohol,2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-ethoxyacetamide(the present compound 1-111) was obtained by the similar method ofProduction Example 9.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.77 (1H, br), 8.30 (1H, dd, J=8.3, 0.97Hz), 7.2-7.4 (4H, m), 7.1-7.2 (1H, m), 7.0-7.1 (3H, m), 6.93 (1H, dd,J=1.9, 8.3 Hz), 6.89 (1H, d, J=1.9 Hz), 5.02 (1H, s), 4.08 (1H, dd,J=2.4, 15.6 Hz), 3.95 (3H, s), 3.91 (1H, dd, J=2.4, 15.6 Hz), 3.89 (3H,s), 2.46 (1H, t, J=2.4 Hz)

PRODUCTION EXAMPLE 14

From2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand isopropyl alcohol,2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-isopropoxyacetamide(the present compound 1-252) was obtained by the similar method ofProduction Example 9.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.94 (1H, br), 8.39 (1H, d, J=8.3 Hz),7.1-7.4 (7H, m), 6.8-7.1 (3H, m), 4.78 (1H, s), 3.95 (3H, s), 3.89 (3H,s), 3.5-3.6 (1H, m), 0.96 (3H, d, J=6.1 Hz), 0.92 (3H, d, J=6.0 Hz)

PRODUCTION EXAMPLE 15

From2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand 2,2,2-trifluoroethyl alcohol,2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-(2,2,2-trifluoroethoxy)acetamide(the present compound 1-234) was obtained by the similar method ofProduction Example 9.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.60 (1H, br), 8.31 (1H, d, J=7.5), 7.2-7.4(6H, m), 7.1-7.2 (1H, m), 6.98 (1H, d, J=8.0 Hz), 6.90 (1H, dd, J=1.9,8.0 Hz), 6.82 (1H, d, J=1.9 Hz), 4.87 (1H, s), 3.95 (3H, s), 3.87 (3H,s), 3.6-3.8 (2H, s)

PRODUCTION EXAMPLE 16

From2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand 2-butyn-1-ol,2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-(2-butynyloxy)acetamide(the present compound 1-241) was obtained by the similar method ofProduction Example 9.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.76 (1H, br), 8.34 (1H, d, J=8.4), 7.2-7.4(6H, m), 7.1-7.2 (1H, m), 6.99 (1H, d, J=8.0 Hz), 6.93 (1H, dd, J=1.9,8.0 Hz), 6.89 (1H, d, J=1.9 Hz), 5.03 (1H, s), 4.0-4.1 (1H, m), 3.96(3H, s), 3.8-3.9 (1H, m), 3.90 (3H, s), 1.81 (3H, t, J=2.0 Hz)

PRODUCTION EXAMPLE 17

In 5 ml of tetrahydrofuran were dissolved 398 mg of2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand 131 mg of triethylamine, 94 mg of acetyl chloride was addeddropwise. The mixture was stirred at room temperature for 1 hour and 30minutes. After addition of water, the reaction mixture was extractedwith ethyl acetate. The organic layer was washed with 5% hydrochloricacid and saturated sodium chloride aqueous solution, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure.The residue was washed with N-hexane, subjected to filtration, and driedto obtain 403 mg of2-acetyloxy-2-(4-chlorophenyl)-N-(3′,4′-dimethoxybiphenyl-2-yl)acetamide(the present compound 1-202)

¹H-NMR (CDCl₃, TMS) d (ppm): 8.35 (1H, d, J=8.3 Hz), 8.06 (1H, br),7.1-7.4 (7H, m), 6.96 (1H, d, J=8.0 Hz), 6.85 (1H, dd, J=1.8, 8.1 Hz),6.82 (1H, d, J=1.7 Hz), 6.03 (1H, s), 3.95 (3H, s), 3.87 (3H, s), 1.92(3H, s)

PRODUCTION EXAMPLE 18

From2-(4-chlorophenyl)-N-(3′,4′-dimethoxybiphenyl-2-yl)-2-hydroxyacetamideand 2-methylpropionic chloride,2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-isobutyryloxyacetamide(the present compound 1-210) was obtained by the similar method ofProduction Example 12.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.35 (1H, d, J=8.0 Hz), 8.09 (1H, br),7.2-7.5 (7H, m), 7.1-7.4 (7H, m), 6.95 (1H, d, J=8.0 Hz), 6.86 (1H, dd,J=1.9, 8.0 Hz), 6.82 (1H, d, J=1.9 Hz), 6.03 (1H, s), 3.95 (3H, s), 3.86(3H, s)2.3-2.4 (1H, m), 1.01 (6H, d, J=6.8 Hz)

PRODUCTION EXAMPLE 19

From2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-hydroxyacetamideand 2,2-dimethylpropionic chloride, 403 mg of2-(4-chlorophenyl)-N-(3′,4′-dihydroxybiphenyl-2-yl)-2-pyvaloyloxyacetamide(the present compound 1-214) was obtained by the similar method ofProduction Example 12.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.34 (1H, d, J=8.4 Hz), 7.98 (1H, br),7.1-7.4 (7H, m)6.95 (1H, d, J=8.3 Hz), 6.86 (1H, dd, J=1.9, 8.3 Hz),6.81 (1H, d, J=1.7 Hz), 6.03 (1H, s), 3.95 (3H, s), 3.84 (3H, s), 1.00(9H, s)

PRODUCTION EXAMPLE 27

In 30 ml of tetrahydrofuran were added 1.75 g ofN-(3′,4′-dimethoxybiphenyl-2-yl)-2-hyrdoxy-2-(4-methylphenyl)acetamideand 0.78 ml of triethylamine, and 0.38ml of methanesulfonyl chloride wasadded dropwise. The mixture was stirred at room temperature for 30minutes. After addition of water, the reaction mixture was extractedwith ethyl acetate. The organic layer was washed with water andsaturated sodium chloride aqueous solution, dried over magnesiumsulfate, and concentrated under reduced pressure. The obtained residueand 10ml of methanol were mixed, and stirred at about 65° C. for 1 hour.The reaction mixture was cooled to room temperature, concentrated underreduced pressure, and extracted with ethyl acetate after addition ofwater. The organic layer was washed with water, dried over magnesiumsulfate, and concentrated under reduced pressure. The residue wassubjected to silica gel column chromatography to obtain 1.3 g ofN-(3′,4′-dimethoxybiphenyl-2-yl)-2-methoxy-2-(4-methylphenyl)acetamide(the present compound 1-006).

¹H-NMR (CDCl₃, TMS) d (ppm): 8.36 (1H, s), 8.35-8.37 (1H, m), 7.12-7.34(7H, m), 6.99 (1H, d, J=8.0 Hz), 6.88-6.93 (2H, m), 4.60 (1H, s), 3.94(3H, s), 3.89 (3H, s), 3.22 (3H, s), 2.33 (3H, s)

Next, the production examples of intermediate of the present compoundare shown as the reference production example.

REFERENCE PRODUCTION EXAMPLE 1

In a mixture of 8.00 g of aluminum chloride and 80 ml of dichloromethanewas added 7.85 g of ethyl oxalyl chloride dropwide at 0° C. overstirring. After addition of 4.60 g of toluene at the same temperature,the mixture was stirred for 1 hour. The reaction mixture was poured inice water, and extracted with chloroform. The organic layer was washedtwo times with saturated sodium chloride aqueous solution, dried overmagnesium sulfate, and concentrated under reduced pressure to obtain 9.3g of ethyl 2-(4-methylphenyl)-2-oxoacetate in crude form.

¹H-NMR (CDCl₃, TMS) d (ppm): 7.91 (2H, d, J=8.2 Hz), 7.31 (2H, d, J=8.1Hz), 4.44 (2H, q, J=7.1 Hz), 2.44 (3H, s), 1.42 (2H, t, J=7.0 Hz)

REFERENCE PRODUCTION EXAMPLE 2

9.3 g of ethyl 2-(4-methylphenyl)-2-oxoacetate, 13 ml of 30% sodiumhydroxide aqueous solution and 15 ml of ethanol were mixed, and heatedunder reflux condition for 2 hours. The reaction mixture was cooled toroom temperature, acidified by addition of 5% hydrochloric acid, andextracted with ethyl acetate. The organic layer was washed two timeswith saturated sodium chloride aqueous solution, dried over magnesiumsulfate, and concentrated under reduced pressure. The residue was washedwith hexane, dried to obtain 5.2g of 2-(4-methylphenyl)-2-oxoaceticacid.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.25 (2H, d, J=8.3 Hz), 7.32 (2H, d, J=8.0Hz), 4.28 (1H, br), 2.45 (3H, s)

REFERENCE PRODUCTION EXAMPLE 3

In 20 ml of toluene were added 2.08 g of 2-(4-methylphenyl)-2-oxoaceticacid, 1.5 ml of thionyl chloride and 49 mg of N,N-dimethylformamide, andstirred at 80° C. for 30 minutes and at 100° C. for 30 minutes. Thereaction mixture was cooled to room temperature, concentrated underreduce pressure to obtain 2-(4-methylphenyl)-2-oxoacetic chloride. Theobtained 2-(4-methylphenyl)-2-oxoacetic chloride was added at 0 to 5° C.in the solution dissolved 2.91 g of 3′,4′-dimethoxy-2-aminobiphenyl and2.6 ml of triethylamine in 30 ml of tetrahydrofuran, stirred at roomtemperature for 2 hours. After addition of water, the reaction mixturewas extracted with ethyl acetate. The organic layer was washed with 5%hydrochloric acid, saturated sodium bicarbonate aqueous solution andsaturated sodium chloride aqueous solution successively, dried overmagnesium sulfate, and concentrated under reduced pressure to obtain3.57 g ofN-(3′,4′-dimethoxybiphenyl-2-yl)-2-(4-methylphenyl)-2-oxoacetamide.

¹H-NMR (CDCl₃, TMS) d (ppm): 9.28 (1H, s), 8.56 (1H, d, J=7.2 Hz), 8.29(2H, d, J=8.4 Hz), 7.40-7.44 (m, 1H), 7.22-7.35 (4H, m), 6.93-7.02 (m,3H), 3.96 (3H, s), 3.91 (3H, s), 2.43 (3H, s)

REFERENCE PRODUCTION EXAMPLE 4

In 10 ml of ethanol was dissolved 0.60 g ofN-(3′,4′-dimethoxybiphenyl-2-yl)-2-(4-methylphenyl)-2-oxoacetamide, and0.12 g of sodium borohydride was added. The mixture was stirred at roomtemperature for 4 hours, and then extracted with ethyl acetate afteraddition of water and 5% hydrochloric acid. The organic layer was washedwith water, saturated sodium bicarbonate aqueous solution and saturatedsodium chloride aqueous solution successively, dried over magnesiumsulfate, and concentrated under reduced pressure. The residue wassubjected to silica gel column chromatography to obtain 285 mg ofN-(3′,4′-dimethoxybiphenyl-2-yl)-2-hyrdoxy-2-(4-methylphenyl)acetamide.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.37 (1H, d, J=4.4 Hz), 7.91 (1H, s),7.32-7.37 (1H, m), 7.01-7.26 (m, 6H), 6.85 (1H, d, J=8.0 Hz), 6.70 (1H,dd, J=8.0, 2.0 Hz), 6.66 (1H, d, J=2.0 Hz), 4.98 (1H, d, J=3 Hz), 3.96(3H, s), 3.79 (3H, s), 3.51 (1H, d, J=3 Hz), 2.34 (3H, s)

REFERENCE PRODUCTION EXAMPLE 5

In 150 ml of toluene were added 15.0 g of 2-(4-methylphenyl)-2-oxoaceticacid, 10.7 ml of thionyl chloride and 0.3 ml of N,N-dimethylformamide,and stirred at 80° C. for 30 minutes and at 100° C. for 30 minutes. Thereaction mixture was cooled to room temperature, and concentrated underreduced pressure to obtain 2-(4-methylphenyl)-2-oxoacetic chloride incrude form. Another hand, in 150 ml of tetrahydrofuran were dissolved15.7 g of 2-bromaniline and 19 ml of triethylamine, and the2-(4-methylphenyl)-2-oxoacetic chloride was added at 0 to 5° C. Themixture was stirred at room temperature for 3 hours. After addition ofwater, the reaction mixture was extracted with ethyl acetate. Theorganic layer was washed with 5% hydrochloric acid, saturated sodiumbicarbonate aqueous solution and saturated sodium chloride aqueoussolution successively, dried over magnesium sulfate, and concentratedunder reduced pressure. The residue was washed with hexane to obtain21.9 g of N-(2-bromophenyl)-2-(4-methylphenyl)-2-oxoacetamide.

¹H-NMR (CDCl₃, TMS) d (ppm): 9.60 (1H, s), 8.51 (1H, dd, J=8.4, 1.2 Hz),8.39 (2H, d, J=8.4 Hz), 7.61 (1H, dd, J=8.0, 1.2 Hz), 7.31-7.41 (3H, m),7.04-7.26 (m, 1H), 2.46 (3H, s)

REFERENCE PRODUCTION EXAMPLE 6

In 100 ml of ethanol were added 10.0 g ofN-(2-bromophenyl)-2-(4-methylphenyl)-2-oxoacetamide and 0.36 g sodiumborohydride, and stirred at room temperature for 8 hours. After additionof saturated ammonium chloride aqueous solution, the reaction mixturewas concentrated under reduced pressure, and extracted with ethylacetate. The organic layer was washed with saturated sodium chlorideaqueous solution, dried over magnesium sulfate, and concentrated toobtain 10.56 g ofN-(2-bromophenyl)-2-hyrdoxy-2-(4-methylphenyl)acetamide.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.70 (1H, s), 8.36 (1H, dd, J=8.4, 1.6 Hz),7.52 (1H, dd, J=8.0, 1.2 Hz), 7.40 (2H, d, J=8.0 Hz), 7.19-7.32 (3H, m),6.96-7.00 (m, 1H), 5.22 (1H, d, J=1.6 Hz), 3.30 (1H, s), 2.36 (3H, s)

REFERENCE PRODUCTION EXAMPLE 7

In 25 ml of ethylene glycol dimethyl ether were added 2.33 g ofN-(2-bromophenyl)-2-hyrdoxy-2-(4-methylphenyl)acetamide, 2.0 g of2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenol, 4.6 g ofpotassium phosphate hydrate and 0.18 g of{1,1′-bis(diphenylphosphino)ferrocene}palladium(II) dichloride(II)methylene chloride complex, and stirred under nitrogen atmosphere at 80°C. for 3 hours. The reaction mixture was cooled at room temperature, andfiltered. The filtrate was concentrated under reduced pressure. Theresidue was subjected to silica gel column chromatography to obtain 2.6g ofN-(3′-methoxy-4′-hydroxybiphenyl-2-yl)-2-hyrdoxy-2-(4-methylphenyl)acetamide.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.36 (1H, d, J=8.4 Hz), 7.88 (1H, s),7.32-7.35 (1H, m), 7.01-7.26 (m, 6H), 6.88 (1H, d, J=7.6 Hz), 6.61-6.64(2H, m), 5.70 (1H, s), 4.98 (1H, d, J=2.8 Hz), 3.79 (3H, s), 3.61-3.63(1H, m), 2.35 (3H, s)

REFERENCE PRODUCTION EXAMPLE 8

In 140 ml of tetrahydrofuran were added 40.0 g of 4-bromochlorobenzeneand 5.33 g of magnesium under nitrogen atmosphere, and stirred toprepare Grignard reagent. In 750 ml of tetrahydrofuran was dissolved49.3 g of diethyl oxalyl, and the Grignard reagent was added dropwise at−70° C. over 30 minutes. The reaction mixture was warmed to roomtemperature over 2 hours, and stirred at room temperature for 2 hours.After addition of ice water and saturated ammonium chloride aqueoussolution, the organic solvent was removed by distillation under reducepressure from the reaction mixture. The residue was filtered, and thefiltrate was extracted with ethyl acetate. The organic layer was washedwith saturated sodium chloride aqueous solution, dried over magnesiumsulfate, and concentrated under reduced pressure. The residue wassubjected to silica gel column chromatography to obtain 22.1 g of ethyl2-(4-chlorophenyl)-2-oxoacetate.

¹H-NMR (CDCl₃, TMS) d (ppm): 7.98-8.01 (2H, m), 7.48-7.51 (2H, m), 3.98(3H, s)

REFERENCE PRODUCTION EXAMPLE 9

In 300 ml of ethanol were added 12.2 g of 2-(4-chlorophenyl)-2-oxoethylacetate and 12.6 g of 20% sodium hydroxide aqueous solution, and stirredat room temperature for 3 hours. The reaction mixture was acidified byaddition of 36% hydrochloric acid, and extracted three times withchloroform. The organic layer was dried over anhydrous magnesiumsulfate, and concentrated under reduced pressure. The residue was washedwith hexane, and dried to obtain 5.2 g of 2-(4-chlorophenyl)-2-oxoaceticacid.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.36-8.39 (1H, m), 8.0 (1H, br), 7.51-7.54(2H, m)

REFERENCE PRODUCTION EXAMPLE 10

In 12 ml of 1,4-dioxane were dissolved 1.12 g of2-(4-chlorophenyl)-2-oxoacetic acid and 3 ml of N,N-dimethylformamide,and 1.18 g of 1,1′-carbonyldiimidazole was added at about 0° C. overstirring. After the mixture was stirred for 1.5 hours, 1.39 g of3′,4′-dimethoxybiphenyl-2-ylamine was added dropwise in the mixture, andstirred at 0° C. for 30 minutes and at room temperature for 2 hours. Thereaction mixture was extracted two times with ethyl acetate afteraddition of water. The organic layer was washed with 5% hydrochloricacid and saturated sodium chloride aqueous solution, dried overmagnesium sulfate, and concentrated under reduced pressure. The residuewas washed with N-hexane, subjected to filtration, and dried to obtain1.44 g of2-(4-chlorophenyl)-N-(3′,4′-dimethoxybiphenyl-2-yl)-2-oxoacetamide.

¹H-NMR (CDCl₃, TMS) d (ppm): 9.30 (1H, br), 8.53 (1H, d, J=8.3 Hz), 8.36(2H, d, J=8.5 Hz), 7.2-7.4 (5H, m), 6.9-7.1 (3H, m), 3.96 (3H, s), 3.91(3H, s)

REFERENCE PRODUCTION EXAMPLE 11

In 15 ml of methanol were dissolved 1.44 g of2-(4-chlorophenyl)-N-(3′,4′-dimethoxybiphenyl-2-yl)-2-oxoacetamide, and69 mg of sodium borohydride was added at about 0° C. After stirring for1.5 hour, the reaction mixture was concentrated under reduced pressure.The obtained residue was extracted with ethyl acetate after addition ofwater. The organic layer was washed with 5% hydrochloric acid andsaturated sodium chloride aqueous solution (two times) successively,dried over anhydrous magnesium sulfate, and concentrated under reducedpressure. The residue was subjected to silica gel column chromatography,and the obtained solid was washed with hexane to obtain 0.70 g of2-(4-chlorophenyl)-N-(3′,4′-dimethoxybiphenyl-2-yl)-2-hydroxyacetamide.

¹H-NMR (CDCl₃, TMS) d (ppm): 8.33 (1H, d, J=8.3 Hz), 7.95 (1H, br),7.1-7.4 (7H, m), 6.83 (1H, d, J=8.0 Hz), 6.71 (1H, d, J=1.9 Hz), 6.65(1H, dd, J=2.0, 7.9 Hzm), 4.99 (1H, br), 3.96 (3H, s), 3.82 (3H, s),3.70 (1H, br)

REFERENCE PRODUCTION EXAMPLE 12

In 100 ml of ethylene glycol dimethyl ether were added 10.1 g of2-bromonitrobenzene, 10.0 g of 3,4-dimethoxyphenylboric acid, 31.8 g ofpotassium phosphate hydrate and 817 mg of{1,1′-bis(diphenylphosphino)ferrocene}palladium(II) dichloride(II)methylene chloride complex, and stirred under nitrogen atmosphere at 80°C. for 4.5 hours. The reaction mixture was cooled to room temperature,and subjected to filtration. The filtrate was concentrated under reducedpressure. The residue was subjected to silica gel column chromatographyto obtain 10.0 g of 3,4-dimethoxy-2′-nitrobiphenyl.

¹H-NMR (CDCl₃, TMS) d (ppm): 7.4-7.9 (4H, m), 6.92 (1H, d, J=8.3 Hz),6.88 (1H, dd, J=1.9, 8.3 Hz), 6.83 (1H, d, J=1.9 Hz), 3.91 (3H, s), 3.88(3H, s)

REFERENCE PRODUCTION EXAMPLE 13

In 100 ml of toluene were added 10.0 g of 3,4-dimethoxy-2′-nitrobiphenyland 0.30 g of 5% Pt/C, furthermore 5.74g of hydrazine hydrate was addedat 80 to 100° C., and stirred at the same temperature for 2 hours. Thereaction mixture was cooled at room temperature, and filtered withCelite (registered trade name) after addition of toluene and water. Thefiltrate was separated, and the organic layer was concentrated underreduced pressure. The residue was washed with hexane, and collected byfiltration to obtain 8.47 g of 3′,4′-dimethoxy-biphenyl-2-ylamine.

¹H-NMR (CDCl₃, TMS) d (ppm): 7.1-7.2 (2H, m), 6.9-7.1 (3H, m), 6.7-6.8(2H, m) 3.92 (3H, s), 3.89 (3H, s), 3.77 (2H, br)

Next, examples of the present compound is shown with a numbers of thepresent compound.

The compound of the following formula wherein R³, R⁴, R⁵, R¹¹, R¹², R¹³,R¹⁴, R¹⁵, R¹⁶ and R¹⁷ in formula (1are hydrogen atoms, and R¹, R², R⁶,R⁷, R⁸, R⁹, R¹⁰, X¹ and X² are the atom or group described in Table 1.TABLE 1

Number R¹ R² R⁶ R⁷ R⁸ R⁹ R¹⁰ X¹ X² 1-001 H H CH₃ H H OCH₃ OCH₃ O O 1-002F H CH₃ H H OCH₃ OCH₃ O O 1-003 Cl H CH₃ H H OCH₃ OCH₃ O O 1-004 Br HCH₃ H H OCH₃ OCH₃ O O 1-005 I H CH₃ H H OCH₃ OCH₃ O O 1-006 CH₃ H CH₃ HH OCH₃ OCH₃ O O 1-007 CH₂CH₃ H CH₃ H H OCH₃ OCH₃ O O 1-008 CH₂CH₂CH₂ HCH₃ H H OCH₃ OCH₃ O O 1-009 CH(CH₃)₂ H CH₃ H H OCH₃ OCH₃ O O 1-010 CH₂FH CH₃ H H OCH₃ OCH₃ O O 1-011 CHF₂ H CH₃ H H OCH₃ OCH₃ O O 1-012 CF₃ HCH₃ H H OCH₃ OCH₃ O O 1-013 CH₂CH₂F H CH₃ H H OCH₃ OCH₃ O O 1-014CH₂CHF₂ H CH₃ H H OCH₃ OCH₃ O O 1-015 CH₂CF₃ H CH₃ H H OCH₃ OCH₃ O O1-016 CHFCF₃ H CH₃ H H OCH₃ OCH₃ O O 1-017 CF₂CF₃ H CH₃ H H OCH₃ OCH₃ OO 1-018 CH═CH₂ H CH₃ H H OCH₃ OCH₃ O O 1-019 C(CH₃)═CH₂ H CH₃ H H OCH₃OCH₃ O O 1-020 CH═CHCH₃ H CH₃ H H OCH₃ OCH₃ O O 1-021 C≡CH H CH₃ H HOCH₃ OCH₃ O O 1-022 C≡CCH₃ H CH₃ H H OCH₃ OCH₃ O O 1-023 OCH₃ H CH₃ H HOCH₃ OCH₃ O O 1-024 OCH₂CH₃ H CH₃ H H OCH₃ OCH₃ O O 1-025 OCH₂CH₂CH₃ HCH₃ H H OCH₃ OCH₃ O O 1-026 OCH(CH₃)₂ H CH₃ H H OCH₃ OCH₃ O O 1-027OCH₂F H CH₃ H H OCH₃ OCH₃ O O 1-028 OCHF₂ H CH₃ H H OCH₃ OCH₃ O O 1-029OCF₃ H CH₃ H H OCH₃ OCH₃ O O 1-030 SCH₃ H CH₃ H H OCH₃ OCH₃ O O 1-031SCH₂CH₃ H CH₃ H H OCH₃ OCH₃ O O 1-032 SCH₂CH₂CH₃ H CH₃ H H OCH₃ OCH₃ O O1-033 SCH(CH₃)₂ H CH₃ H H OCH₃ OCH₃ O O 1-034 SCH₂F H CH₃ H H OCH₃ OCH₃O O 1-035 SCHF₂ H CH₃ H H OCH₃ OCH₃ O O 1-036 SCF₃ H CH₃ H H OCH₃ OCH₃ OO 1-037 c-Pr H CH₃ H H OCH₃ OCH₃ O O 1-038 H F CH₃ H H OCH₃ OCH₃ O O1-039 H Cl CH₃ H H OCH₃ OCH₃ O O 1-040 H Br CH₃ H H OCH₃ OCH₃ O O 1-041H CH₃ CH₃ H H OCH₃ OCH₃ O O 1-042 H OCH₃ CH₃ H H OCH₃ OCH₃ O O 1-043 ClF CH₃ H H OCH₃ OCH₃ O O 1-044 Cl Cl CH₃ H H OCH₃ OCH₃ O O 1-045 Cl BrCH₃ H H OCH₃ OCH₃ O O 1-046 Cl CH₃ CH₃ H H OCH₃ OCH₃ O O 1-047 Cl OCH₃CH₃ H H OCH₃ OCH₃ O O 1-048 Br F CH₃ H H OCH₃ OCH₃ O O 1-049 Br Cl CH₃ HH OCH₃ OCH₃ O O 1-050 Br Br CH₃ H H OCH₃ OCH₃ O O 1-051 Br CH₃ CH₃ H HOCH₃ OCH₃ O O 1-052 Br OCH₃ CH₃ H H OCH₃ OCH₃ O O 1-053 CH₃ F CH₃ H HOCH₃ OCH₃ O O 1-054 CH₃ Cl CH₃ H H OCH₃ OCH₃ O O 1-055 CH₃ Br CH₃ H HOCH₃ OCH₃ O O 1-056 CH₃ CH₃ CH₃ H H OCH₃ OCH₃ O O 1-057 CH₃ OCH₃ CH₃ H HOCH₃ OCH₃ O O 1-058 H H CH₂C≡CH H H OCH₃ OCH₃ O O 1-059 F H CH₂C≡CH H HOCH₃ OCH₃ O O 1-060 Cl H CH₂C≡CH H H OCH₃ OCH₃ O O 1-061 Br H CH₂C≡CH HH OCH₃ OCH₃ O O 1-062 I H CH₂C≡CH H H OCH₃ OCH₃ O O 1-063 CH₃ H CH₂C≡CHH H OCH₃ OCH₃ O O 1-064 CH₂CH₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-065CH₂CH₂CH₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-066 CH(CH₃)₂ H CH₂C≡CH H H OCH₃OCH₃ O O 1-067 CH₂F H CH₂C≡CH H H OCH₃ OCH₃ O O 1-068 CHF₂ H CH₂C≡CH H HOCH₃ OCH₃ O O 1-069 CF₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-070 CH₂CH₂F HCH₂C≡CH H H OCH₃ OCH₃ O O 1-071 CH₂CHF₂ H CH₂C≡CH H H OCH₃ OCH₃ O O1-072 CH₂CF₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-073 CHFCF₃ H CH₂C≡CH H H OCH₃OCH₃ O O 1-074 CF₂CF₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-075 CH═CH₂ H CH₂C≡CHH H OCH₃ OCH₃ O O 1-076 C(CH₃)═CH₂ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-077CH═CCH₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-078 C≡CH H CH₂C≡CH H H OCH₃ OCH₃ OO 1-079 C≡CCH₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-080 OCH₃ H CH₂C≡CH H H OCH₃OCH₃ O O 1-081 OCH₂CH₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-082 OCH₂CH₂CH₃ HCH₂C≡CH H H OCH₃ OCH₃ O O 1-083 OCH(CH₃)₂ H CH₂C≡CH H H OCH₃ OCH₃ O O1-084 OCH₂F H CH₂C≡CH H H OCH₃ OCH₃ O O 1-085 OCHF₂ H CH₂C≡CH H H OCH₃OCH₃ O O 1-086 OCF₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-087 SCH₃ H CH₂C≡CH H HOCH₃ OCH₃ O O 1-088 SCH₂CH₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-089 SCH₂CH₂CH₃H CH₂C≡CH H H OCH₃ OCH₃ O O 1-090 SCH(CH₃)₂ H CH₂C≡CH H H OCH₃ OCH₃ O O1-091 SCH₂F H CH₂C≡CH H H OCH₃ OCH₃ O O 1-092 SCHF₂ H CH₂C≡CH H H OCH₃OCH₃ O O 1-093 SCF₃ H CH₂C≡CH H H OCH₃ OCH₃ O O 1-094 c-Pr H CH₂C≡CH H HOCH₃ OCH₃ O O 1-095 H F CH₂C≡CH H H OCH₃ OCH₃ O O 1-096 H Cl CH₂C≡CH H HOCH₃ OCH₃ O O 1-097 H Br CH₂C≡CH H H OCH₃ OCH₃ O O 1-098 H CH₃ CH₂C≡CH HH OCH₃ OCH₃ O O 1-099 H OCH₃ CH₂C≡CH H H OCH₃ OCH₃ O O 1-100 Cl FCH₂C≡CH H H OCH₃ OCH₃ O O 1-101 Cl Cl CH₂C≡CH H H OCH₃ OCH₃ O O 1-102 ClBr CH₂C≡CH H H OCH₃ OCH₃ O O 1-103 Cl CH₃ CH₂C≡CH H H OCH₃ OCH₃ O O1-104 Cl OCH₃ CH₂C≡CH H H OCH₃ OCH₃ O O 1-105 Br F CH₂C≡CH H H OCH₃ OCH₃O O 1-106 Br Cl CH₂C≡CH H H OCH₃ OCH₃ O O 1-107 Br Br CH₂C≡CH H H OCH₃OCH₃ O O 1-108 Br CH₃ CH₂C≡CH H H OCH₃ OCH₃ O O 1-109 Br OCH₃ CH₂C≡CH HH OCH₃ OCH₃ O O 1-110 H H CH₂CH₃ H H OCH₃ OCH₃ O O 1-111 Cl H CH₂CH₃ H HOCH₃ OCH₃ O O 1-112 Br H CH₂CH₃ H H OCH₃ OCH₃ O O 1-113 CH₃ H CH₂CH₃ H HOCH₃ OCH₃ O O 1-114 CH₂CH₃ H CH₂CH₃ H H OCH₃ OCH₃ O O 1-115 OCH₃ HCH₂CH₃ H H OCH₃ OCH₃ O O 1-116 CF₃ H CH₂CH₃ H H OCH₃ OCH₃ O O 1-117 H HCH₂CH₂CH₃ H H OCH₃ OCH₃ O O 1-118 Cl H CH₂CH₂CH₃ H H OCH₃ OCH₃ O O 1-119Br H CH₂CH₂CH₃ H H OCH₃ OCH₃ O O 1-120 CH₃ H CH₂CH₂CH₃ H H OCH₃ OCH₃ O O1-121 CH₂CH₃ H CH₂CH₂CH₃ H H OCH₃ OCH₃ O O 1-122 OCH₃ H CH₂CH₂CH₃ H HOCH₃ OCH₃ O O 1-123 CF₃ H CH₂CH₂CH₃ H H OCH₃ OCH₃ O O 1-124 H H CH₂F H HOCH₃ OCH₃ O O 1-125 Cl H CH₂F H H OCH₃ OCH₃ O O 1-126 Br H CH₂F H H OCH₃OCH₃ O O 1-127 CH₃ H CH₂F H H OCH₃ OCH₃ O O 1-128 CH₂CH₃ H CH₂F H H OCH₃OCH₃ O O 1-129 OCH₃ H CH₂F H H OCH₃ OCH₃ O O 1-130 CF₃ H CH₂F H H OCH₃OCH₃ O O 1-131 H H CH₂F H H OCH₃ OCH₃ O O 1-132 Cl H CH₂F H H OCH₃ OCH₃O O 1-133 Br H CH₂F H H OCH₃ OCH₃ O O 1-134 CH₃ H CH₂F H H OCH₃ OCH₃ O O1-135 CH₂CH₃ H CH₂F H H OCH₃ OCH₃ O O 1-136 OCH₃ H CH₂F H H OCH₃ OCH₃ OO 1-137 CF₃ H CH₂F H H OCH₃ OCH₃ O O 1-138 H H CF₃ H H OCH₃ OCH₃ O O1-139 Cl H CF₃ H H OCH₃ OCH₃ O O 1-140 Br H CF₃ H H OCH₃ OCH₃ O O 1-141CH₃ H CF₃ H H OCH₃ OCH₃ O O 1-142 CH₂CH₃ H CF₃ H H OCH₃ OCH₃ O O 1-143OCH₃ H CF₃ H H OCH₃ OCH₃ O O 1-144 CF₃ H CF₃ H H OCH₃ OCH₃ O O 1-145 H HCH₂═CH₂ H H OCH₃ OCH₃ O O 1-146 Cl H CH₂═CH₂ H H OCH₃ OCH₃ O O 1-147 BrH CH₂═CH₂ H H OCH₃ OCH₃ O O 1-148 CH₃ H CH₂═CH₂ H H OCH₃ OCH₃ O O 1-149CH₂CH₃ H CH₂═CH₂ H H OCH₃ OCH₃ O O 1-150 OCH₃ H CH₂═CH₂ H H OCH₃ OCH₃ OO 1-151 CF₃ H CH₂═CH₂ H H OCH₃ OCH₃ O O 1-152 H H CH₃ H H OCH₃ OCH₃ O O1-153 Cl H CH₃ H CH₃ OCH₃ OCH₃ O O 1-154 Br H CH₃ H CH₃ OCH₃ OCH₃ O O1-155 CH₃ H CH₃ H CH₃ OCH₃ OCH₃ O O 1-156 CH₂CH₃ H CH₃ H CH₃ OCH₃ OCH₃ OO 1-157 OCH₃ H CH₃ H CH₃ OCH₃ OCH₃ O O 1-158 CF₃ H CH₃ H CH₃ OCH₃ OCH₃ OO 1-159 H H CH₂C≡CH H CH₃ OCH₃ OCH₃ O O 1-160 Cl H CH₂C≡CH H CH₃ OCH₃OCH₃ O O 1-161 Br H CH₂C≡CH H CH₃ OCH₃ OCH₃ O O 1-162 CH₃ H CH₂C≡CH HCH₃ OCH₃ OCH₃ O O 1-163 CH₂CH₃ H CH₂C≡CH H CH₃ OCH₃ OCH₃ O O 1-164 OCH₃H CH₂C≡CH H CH₃ OCH₃ OCH₃ O O 1-165 CF₃ H CH₂C≡CH H H OCH₃ OCH₃ O O1-166 H H CH₃ H H OCH₃ OCH₃ S O 1-167 Cl H CH₃ H H OCH₃ OCH₃ S O 1-168Br H CH₃ H H OCH₃ OCH₃ S O 1-169 CH₃ H CH₃ H H OCH₃ OCH₃ S O 1-170CH₂CH₃ H CH₃ H H OCH₃ OCH₃ S O 1-171 OCH₃ H CH₃ H H OCH₃ OCH₃ S O 1-172CF₃ H CH₃ H H OCH₃ OCH₃ S O 1-173 H H CH₂C≡CH H H OCH₃ OCH₃ S O 1-174 ClH CH₂C≡CH H H OCH₃ OCH₃ S O 1-175 Br H CH₂C≡CH H H OCH₃ OCH₃ S O 1-176CH₃ H CH₂C≡CH H H OCH₃ OCH₃ S O 1-177 CH₂CH₃ H CH₂C≡CH H H OCH₃ OCH₃ S O1-178 OCH₃ H CH₂C≡CH H H OCH₃ OCH₃ S O 1-179 CF₃ H CH₂C≡CH H H OCH₃ OCH₃S O 1-180 H H CH₃ H H OCH₃ OCH₃ O S 1-181 Cl H CH₃ H H OCH₃ OCH₃ O S1-182 Br H CH₃ H H OCH₃ OCH₃ O S 1-183 CH₃ H CH₃ H H OCH₃ OCH₃ O S 1-184CH₂CH₃ H CH₃ H H OCH₃ OCH₃ O S 1-185 OCH₃ H CH₃ H H OCH₃ OCH₃ O S 1-186CF₃ H CH₃ H H OCH₃ OCH₃ O S 1-187 H H CH₂C≡CH H H OCH₃ OCH₃ O S 1-188 ClH CH₂C≡CH H H OCH₃ OCH₃ O S 1-189 Br H CH₂C≡CH H H OCH₃ OCH₃ O S 1-190CH₃ H CH₂C≡CH H H OCH₃ OCH₃ O S 1-191 CH₂CH₃ H CH₂C≡CH H H OCH₃ OCH₃ O S1-192 OCH₃ H CH₂C≡CH H H OCH₃ OCH₃ O S 1-193 CF₃ H CH₂C≡CH H H OCH₃ OCH₃O S 1-194 H H CH₂C≡CH CH₃ H OCH₃ OCH₃ O O 1-195 Cl H CH₂C≡CH CH₃ H OCH₃OCH₃ O O 1-196 Br H CH₂C≡CH CH₃ H OCH₃ OCH₃ O O 1-197 CH₃ H CH₂C≡CH CH₃H OCH₃ OCH₃ O O 1-198 CH₂CH₃ H CH₂C≡CH CH₃ H OCH₃ OCH₃ O O 1-199 OCH₃ HCH₂C≡CH CH₃ H OCH₃ OCH₃ O O 1-200 CF₃ H CH₂C≡CH CH₃ H OCH₃ OCH₃ O O1-201 H H COCH₃ H H OCH₃ OCH₃ O O 1-202 Cl H COCH₃ H H OCH₃ OCH₃ O O1-203 Br H COCH₃ H H OCH₃ OCH₃ O O 1-204 CH₃ H COCH₃ H H OCH₃ OCH₃ O O1-205 H H COCH₂CH₃ H H OCH₃ OCH₃ O O 1-206 Cl H COCH₂CH₃ H H OCH₃ OCH₃ OO 1-207 Br H COCH₂CH₃ H H OCH₃ OCH₃ O O 1-208 CH₃ H COCH₂CH₃ H H OCH₃OCH₃ O O 1-209 H H COCH(CH₃)₂ H H OCH₃ OCH₃ O O 1-210 Cl H COCH(CH₃)₂ HH OCH₃ OCH₃ O O 1-211 Br H COCH(CH₃)₂ H H OCH₃ OCH₃ O O 1-212 CH₃ HCOCH(CH₃)₂ H H OCH₃ OCH₃ O O 1-213 H H COC(CH₃)₃ H H OCH₃ OCH₃ O O 1-214Cl H COC(CH₃)₃ H H OCH₃ OCH₃ O O 1-215 Br H COC(CH₃)₃ H H OCH₃ OCH₃ O O1-216 CH₃ H COC(CH₃)₃ H H OCH₃ OCH₃ O S 1-217 H H COCH═CH₂ H H OCH₃ OCH₃O S 1-218 Cl H COCH═CH₂ H H OCH₃ OCH₃ O O 1-219 Br H COCH═CH₂ H H OCH₃OCH₃ O O 1-220 CH₃ H COCH═CH₂ H H OCH₃ OCH₃ O O 1-221 H H COC≡CH H HOCH₃ OCH₃ O O 1-222 Cl H COC≡CH H H OCH₃ OCH₃ O O 1-223 Br H COC≡CH H HOCH₃ OCH₃ O O 1-224 CH₃ H COC≡CH H H OCH₃ OCH₃ O O 1-225 H H COCH₂Cl H HOCH₃ OCH₃ O O 1-226 H H CH₂CH₂F H H CH₃ CH₃ O O 1-227 Cl H CH₂CH₂F H HCH₃ CH₃ O O 1-228 Br H CH₂CH₂F H H CH₃ CH₃ O O 1-229 CH₃ H CH₂CH₂F H HCH₃ CH₃ O O 1-230 CH₂CH₃ H CH₂CH₂F H H CH₃ CH₃ O O 1-231 OCH₃ H CH₂CH₂FH H CH₃ CH₃ O O 1-232 CF₃ H CH₂CH₂F H H CH₃ CH₃ O O 1-233 H H CH₂CF₃ H HCH₃ CH₃ O O 1-234 Cl H CH₂CF₃ H H CH₃ CH₃ O O 1-235 Br H CH₂CF₃ H H CH₃CH₃ O O 1-236 CH₃ H CH₂CF₃ H H CH₃ CH₃ O O 1-237 CH₂CH₃ H CH₂CF₃ H H CH₃CH₃ O O 1-238 OCH₃ H CH₂CF₃ H H CH₃ CH₃ O O 1-239 CF₃ H CH₂CF₃ H H CH₃CH₃ O O 1-240 H H CH₂C≡CCH₃ H H CH₃ CH₃ O O 1-241 Cl H CH₂C≡CCH₃ H H CH₃CH₃ O O 1-242 Br H CH₂C≡CCH₃ H H CH₃ CH₃ O O 1-243 CH₃ H CH₂C≡CCH₃ H HCH₃ CH₃ O O 1-244 CH₂CH₃ H CH₂C≡CCH₃ H H CH₃ CH₃ O O 1-245 OCH₃ HCH₂C≡CCH₃ H H CH₃ CH₃ O O 1-246 CF₃ H CH₂C≡CCH₃ H H CH₃ CH₃ O O 1-247 CNH CH₃ H H CH₃ CH₃ O O 1-248 CN H CH₂C≡CCH₃ H H CH₃ CH₃ O O 1-249 CN HCH₃ H H CH₂C≡CCH₃ CH₃ O O 1-250 CN H CH₂C≡CCH₃ H H CH₂C≡CCH₃ CH₃ O O1-251 H H CH(CH₃)₂ H H OCH₃ OCH₃ O O 1-252 Cl H CH(CH₃)₂ H H OCH₃ OCH₃ OO 1-253 Br H CH(CH₃)₂ H H OCH₃ OCH₃ O O 1-254 CH₃ H CH(CH₃)₂ H H OCH₃OCH₃ O O 1-255 CH₂CH₃ H CH(CH₃)₂ H H OCH₃ OCH₃ O O 1-256 OCH₃ H CH(CH₃)₂H H OCH₃ OCH₃ O O 1-257 CF₃ H CH(CH₃)₂ H H OCH₃ OCH₃ O OIn the table, “c-Pr” means cyclopropyl.

In the table, “c-Pr” means cyclopropyl.

The compound of the following formula wherein R², R³, R⁴, R⁵, R⁷, R⁸,R¹¹, R¹² and R¹³ in the formula (1) are hydrogen atoms, and R¹, R⁶, R⁹,R¹⁰, R¹⁴, R¹⁵ R¹⁶ and R¹⁷ are the atom or group described in Table 2.TABLE 2

Number R¹ R⁶ R⁹ R¹⁰ R¹⁴ R¹⁵ R¹⁶ R¹⁷ 2-001 H CH₃ OC₂H₅ OCH₃ H H H H 2-002Cl CH₃ OC₂H₅ OCH₃ H H H H 2-003 Br CH₃ OC₂H₅ OCH₃ H H H H 2-004 CH₃ CH₃OC₂H₅ OCH₃ H H H H 2-005 CH₂CH₃ CH₃ OC₂H₅ OCH₃ H H H H 2-006 OCH₃ CH₃OC₂H₅ OCH₃ H H H H 2-007 CF₃ CH₃ OC₂H₅ OCH₃ H H H H 2-008 H CH₂C≡CHOC₂H₅ OCH₃ H H H H 2-009 Cl CH₂C≡CH OC₂H₅ OCH₃ H H H H 2-010 Br CH₂C≡CHOC₂H₅ OCH₃ H H H H 2-011 CH₃ CH₂C≡CH OC₂H₅ OCH₃ H H H H 2-012 CH₂CH₃CH₂C≡CH OC₂H₅ OCH₃ H H H H 2-013 OCH₃ CH₂C≡CH OC₂H₅ OCH₃ H H H H 2-014CF₃ CH₂C≡CH OC₂H₅ OCH₃ H H H H 2-015 H CH₃ OCH₂C≡CH OCH₃ H H H H 2-016Cl CH₃ OCH₂C≡CH OCH_(3 H) H H H 2-017 Br CH₃ OCH₂C≡CH OCH_(3 H) H H H2-018 CH₃ CH₃ OCH₂C≡CH OCH₃ H H H H 2-019 CH₂CH₃ CH₃ OCH₂C≡CH OCH_(3 H)H H H 2-020 OCH₃ CH₃ OCH₂C≡CH OCH_(3 H) H H H 2-021 CF₃ CH₃ OCH₂C≡CHOCH_(3 H) H H H 2-022 H CH₂C≡CH OCH₂C≡CH OCH₃ H H H H 2-023 Cl CH₂C≡CHOCH₂C≡CH OCH₃ H H H H 2-024 Br CH₂C≡CH OCH₂C≡CH OCH₃ H H H H 2-025 CH₃CH₂C≡CH OCH₂C≡CH OCH₃ H H H H 2-026 CH₂CH₃ CH₂C≡CH OCH₂C≡CH OCH₃ H H H H2-027 OCH₃ CH₂C≡CH OCH₂C≡CH OCH₃ H H H H 2-028 CF₃ CH₂C≡CH OCH₂C≡CH OCH₃H H H H 2-029 H CH₃ OCH₂CN OCH₃ H H H H 2-030 Cl CH₃ OCH₂CN OCH₃ H H H H2-031 Br CH₃ OCH₂CN OCH₃ H H H H 2-032 CH₃ CH₃ OCH₂CN OCH₃ H H H H 2-033CH₂CH₃ CH₃ OCH₂CN OCH₃ H H H H 2-034 OCH₃ CH₃ OCH₂CN OCH₃ H H H H 2-035CF₃ CH₃ OCH₂CN OCH₃ H H H H 2-036 H CH₂C≡CH OCH₂CN OCH₃ H H H H 2-037 ClCH₂C≡CH OCH₂CN OCH₃ H H H H 2-038 Br CH₂C≡CH OCH₂CN OCH₃ H H H H 2-039CH₃ CH₂C≡CH OCH₂CN OCH₃ H H H H 2-040 CH₂CH₃ CH₂C≡CH OCH₂CN OCH₃ H H H H2-041 OCH₃ CH₂C≡CH OCH₂CN OCH₃ H H H H 2-042 CF₃ CH₂C≡CH OCH₂CN OCH₃ H HH H 2-043 Cl CH₃ OCH₃ OCH₃ CH₃ H H H 2-044 CH₃ CH₃ OCH₃ OCH₃ CH₃ H H H2-045 Cl CH₂C≡CH OCH₃ OCH₃ CH₃ H H H 2-046 CH₃ CH₂C≡CH OCH₃ OCH₃ CH₃ H HH 2-047 Cl CH₃ OCH₃ OCH₃ Cl H H H 2-048 CH₃ CH₃ OCH₃ OCH₃ Cl H H H 2-049Cl CH₂C≡CH OCH₃ OCH₃ Cl H H H 2-050 CH₃ CH₂C≡CH OCH₃ OCH₃ Cl H H H 2-051Cl CH₃ OCH₃ OCH₃ OCH_(3 H) H H 2-052 CH₃ CH₃ OCH₃ OCH₃ OCH_(3 H) H H2-053 Cl CH₂C≡CH OCH₃ OCH₃ OCH_(3 H) H H 2-054 CH₃ CH₂C≡CH OCH₃ OCH₃OCH_(3 H) H H 2-055 Cl CH₃ OCH₃ OCH₃ CN H H H 2-056 CH₃ CH₃ OCH₃ OCH₃ CNH H H 2-057 Cl CH₂C≡CH OCH₃ OCH₃ CN H H H 2-058 CH₃ CH₂C≡CH OCH₃ OCH₃ CNH H H 2-059 Cl CH₃ OCH₃ OCH₃ H CH₃ H H 2-060 CH₃ CH₃ OCH₃ OCH₃ H CH₃ H H2-061 Cl CH₂C≡CH OCH₃ OCH₃ H CH₃ H H 2-062 CH₃ CH₂C≡CH OCH₃ OCH₃ H CH₃ HH 2-063 Cl CH₃ OCH₃ OCH₃ H Cl H H 2-064 CH₃ CH₃ OCH₃ OCH₃ H Cl H H 2-065Cl CH₂C≡CH OCH₃ OCH₃ H Cl H H 2-066 CH₃ CH₂C≡CH OCH₃ OCH₃ H Cl H H 2-067Cl CH₃ OCH₃ OCH₃ H OCH₃ H H 2-068 CH₃ CH₃ OCH₃ OCH₃ H OCH₃ H H 2-069 ClCH₂C≡CH OCH₃ OCH₃ H OCH₃ H H 2-070 CH₃ CH₂C≡CH OCH₃ OCH₃ H OCH₃ H H2-071 Cl CH₃ OCH₃ OCH₃ H CN H H 2-072 CH₃ CH₃ OCH₃ OCH₃ H CN H H 2-073Cl CH₂C≡CH OCH₃ OCH₃ H CN H H 2-074 CH₃ CH₂C≡CH OCH₃ OCH₃ H CN H H 2-075Cl CH₃ OCH₃ OCH₃ H H CH₃ H 2-076 CH₃ CH₃ OCH₃ OCH₃ H H CH₃ H 2-077 ClCH₂C≡CH OCH₃ OCH₃ H H CH₃ H 2-078 CH₃ CH₂C≡CH OCH₃ OCH₃ H H CH₃ H 2-079Cl CH₃ OCH₃ OCH₃ H H Cl H 2-080 CH₃ CH₃ OCH₃ OCH₃ H H Cl H 2-081 ClCH₂C≡CH OCH₃ OCH₃ H H Cl H 2-082 CH₃ CH₂C≡CH OCH₃ OCH₃ H H Cl H 2-083 ClCH₃ OCH₃ OCH₃ H H OCH₃ H 2-084 CH₃ CH₃ OCH₃ OCH₃ H H OCH₃ H 2-085 ClCH₂C≡CH OCH₃ OCH₃ H H OCH₃ H 2-086 CH₃ CH₂C≡CH OCH₃ OCH₃ H H OCH₃ H2-087 Cl CH₃ OCH₃ OCH₃ H H CN H 2-088 CH₃ CH₃ OCH₃ OCH₃ H H CN H 2-089Cl CH₂C≡CH OCH₃ OCH₃ H H CN H 2-090 CH₃ CH₂C≡CH OCH₃ OCH₃ H H CN H 2-091Cl CH₃ OCH₃ OCH₃ H H H CH₃ 2-092 CH₃ CH₃ OCH₃ OCH₃ H H H CH₃ 2-093 ClCH₂C≡CH OCH₃ OCH₃ H H H CH₃ 2-094 CH₃ CH₂C≡CH OCH₃ OCH₃ H H H CH₃ 2-095Cl CH₃ OCH₃ OCH₃ H H H Cl 2-096 CH₃ CH₃ OCH₃ OCH₃ H H H Cl 2-097 ClCH₂C≡CH OCH₃ OCH₃ H H H Cl 2-098 CH₃ CH₂C≡CH OCH₃ OCH₃ H H H Cl 2-099 ClCH₃ OCH₃ OCH₃ H H H OCH₃ 2-100 CH₃ CH₃ OCH₃ OCH₃ H H H OCH₃ 2-101 ClCH₂C≡CH OCH₃ OCH₃ H H H OCH₃ 2-102 CH₃ CH₃ OCH₃ OCH₃ H H H CN 2-103 ClCH₂C≡CH OCH₃ OCH₃ H H H CN 2-104 CH₃ CH₂C≡CH OCH₃ OCH₃ H H H CN 2-105 ClCH₂C≡CH OCH₃ OCH₃ Cl Cl H H 2-106 CH₃ CH₂C≡CH OCH₃ OCH₃ Cl Cl H H 2-107Cl CH₂C≡CH OCH₃ OCH₃ Cl H Cl H 2-108 CH₃ CH₂C≡CH OCH₃ OCH₃ Cl H Cl H2-109 Cl CH₂C≡CH OCH₃ OCH₃ Cl H H Cl 2-110 CH₃ CH₂C≡CH OCH₃ OCH₃ Cl H HCl 2-111 Cl CH₂C≡CH OCH₃ OCH₃ H Cl Cl H 2-112 CH₃ CH₂C≡CH OCH₃ OCH₃ H ClCl H 2-113 Cl CH₂C≡CH OCH₃ OCH₃ H H Cl Cl 2-114 CH₃ CH₂C≡CH OCH₃ OCH₃ HH Cl Cl 2-115 Cl CH₂C≡CH OCH₃ OCH₃ CH₃ CH₃ H H 2-116 CH₃ CH₂C≡CH OCH₃OCH₃ CH₃ CH₃ H H 2-117 Cl CH₂C≡CH OCH₃ OCH₃ CH₃ H CH₃ H 2-118 CH₃CH₂C≡CH OCH₃ OCH₃ CH₃ H CH₃ H 2-119 Cl CH₂C≡CH OCH₃ OCH₃ CH₃ H H CH₃2-120 CH₃ CH₂C≡CH OCH₃ OCH₃ CH₃ H H CH₃ 2-121 Cl CH₂C≡CH OCH₃ OCH₃ H CH₃CH₃ H 2-122 CH₃ CH₂C≡CH OCH₃ OCH₃ H CH₃ CH₃ H 2-123 Cl CH₂C≡CH OCH₃ OCH₃H H CH₃ CH₃ 2-124 CH₃ CH₂C≡CH OCH₃ OCH₃ H H CH₃ CH₃ 2-125 Cl CH₂C≡CHOCH₃ OCH₃ CH₃ F H H 2-126 CH₃ CH₂C≡CH OCH₃ OCH₃ CH₃ F H H 2-127 ClCH₂C≡CH OCH₃ OCH₃ Cl H F H 2-128 CH₃ CH₂C≡CH OCH₃ OCH₃ Cl H F H 2-129 ClCH₂C≡CH OCH₃ OCH₃ OCH₃ H H Cl 2-130 CH₃ CH₂C≡CH OCH₃ OCH₃ OCH₃ H H Cl2-131 Cl CH₂C≡CH OCH₃ OCH₃ H F Cl H 2-132 CH₃ CH₂C≡CH OCH₃ OCH₃ H F Cl H2-133 Cl CH₂C≡CH OCH₃ OCH₃ H H OCH₃ CH₃ 2-134 CH₃ CH₂C≡CH OCH₃ OCH₃ H HOCH₃ CH₃ 2-133 Cl CH₂C≡CH OCH₃ OCH₃ CF₃ H H H 2-134 CH₃ CH₂C≡CH OCH₃OCH₃ CF₃ H H H 2-137 Cl CH₂C≡CH OCH₃ OCH₃ H OCF₃ H H 2-138 CH₃ CH₂C≡CHOCH₃ OCH₃ H OCF₃ H H 2-139 Cl CH₂C≡CH OCH₃ OCH₃ H H c-Pr H 2-140 CH₃CH₂C≡CH OCH₃ OCH₃ H H c-Pr H 2-141 Cl CH₂C≡CH OCH₃ OCH₃ H H H SCH₃ 2-142CH₃ CH₂C≡CH OCH₃ OCH₃ H H H SCH₃In the table, “c-Pr” means cyclopropyl.

In the table, “c-Pr” means cyclopropyl.

Next formulation examples are shown. Parts represent parts by weight.The present compounds are described with the above-mentioned numbers.

FORMULATION EXAMPLE 1

Fifty parts of each of the present compounds 1-001 to 1-257 and 2-001 to1-142, 3 parts of calcium ligninsulfonate, 2 parts of magnesiumlaurylsulfate and 45 parts of synthetic hydrated silica are pulverizedand mixed well to give wettable powders of each compound.

FORMULATION EXAMPLE 2

Twenty parts of each of the present compounds 1-001 to 1-257 and 2-001to 1-142 and 1.5 parts of sorbitan trioleate are mixed with 28.5 partsof an aqueous solution containing 2 parts of polyvinyl alcohol, andwet-pulverized finely. To the obtained mixture, 40 parts of an aqueoussolution containing 0.05 part of xanthan gum and 0.1 part of aluminiummagnesium silicate is added and further 10 parts of propylene glycol areadded to give a flowable of each compound.

FORMULATION EXAMPLE 3

Two parts of each of the present compounds 1-001 to 1-257 and 2-001 to1-142, 88 parts of kaolin clay and 10 parts of talc are pulverized andmixed well to give dusts of each compound.

FORMULATION EXAMPLE 4

Five parts of each of the present compounds 1-001 to 1-257 and 2-001 to1-142, 14 parts of polyoxyethylenestyryl phenyl ether, 6 parts ofcalcium dodecylbenzenesulfonate and 75 parts of xylene are mixed well togive emulsifiable concentrates of each compound.

FORMULATION EXAMPLE 5

Two parts of each of the present compounds 1-001 to 1-257 and 2-001 to1-142, 1 part of synthetic hydrated silica, 2 parts of calciumligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay arepulverized and mixed well, and water is added thereto and kneeded,granulated and dried to give granules of each compound.

FORMULATION EXAMPLE 6

Ten parts of each of the present compounds 1-001 to 1-257 and 2-001 to1-142, 35 parts of white carbon containing 50% of ammoniumpolyoxyethylenealkyl ether sulfate and 55 parts of water are mixed andwet pulverized finely to give a formulation of each compound.

Next, it is shown that a present compounds are useful for controllingplant diseases. The present compounds are described with theabove-mentioned numbers.

For comparison, a compound of number 4.1 described in European PatentPublished Application 0545099, namely N- biphenyl-2-yl-2-methylbenzamide(hereinafter, refered to as the comparative compound A), was alsosubjected to the examination.

Additionally, the control effect was evaluated by visually observing thearea of a lesion on a sample plant in investigation and comparing thearea of a lesion on a non-treatment plant and the area of a lesion on atreated plant with the present compound.

TEST EXAMPLE 1

Sand loam was compacted in a plastic pot, and a tomato (variety:Ponterosa) was seeded and grown in a green house for 20 days. Thepresent compounds 1-006, 1-058, 1-059, 1-060, 1-063, 1-064, 1-080,1-098, 1-111, 1-202, 1-210, 1-227, 1-234, 1-252, 2-025. 2-046, 2-062,2-078 and the comparative compound A were formulated according toFormulation Example 6, then, diluted with water to provide givenconcentration of 500ppm, and these were sprayed onto stems and leaves soas to give sufficient adhesion on the surface of the tomato leaves.After spraying, the liquid on the stem was air-dried, and a suspensionof zoosporangiua of Phytophthora infestans was inoculated by spraying.After inoculation, the plant was first grown for one day at 23° C. underhigh humidity, then further grown for 4 days in the green house.

The areas of a lesion of the plants were visually obserbed. The lesionareas on plants on the plants treated with the present compound 1-006,1-058, 1-059, 1-060, 1-063, 1-064, 1-080, 1-098, 1-111, 1-202, 1-210,1-227, 1-234, 1-252, 2-025, 2-046, 2-062 and 2-078 were not more than10% of the lesion area on a non-treatment plant. The lesion areas onplants on the plants treated with the comparative compound A was in arange of 76 to 100% of the lesion area on a non-treatment plant.

TEST EXAMPLE 2

Sand loam was compacted in a plastic pot, and a grape (variety: Berry A)was seeded and grown in a green house for 40 days. The present compounds1-003, 1-006, 1-058, 1-059, 1-060, 1-063, 1-064, 1-080, 1-098, 1-111,1-210, 1-214, 1-227, 1-252, 2-025, 2-046, 2-062 and 2-078 wereformulated according to Formulation Example 6, then, diluted with waterto provide given concentration of 200 ppm, and these were sprayed ontostems and leaves so as to give sufficient adhesion on the surface ofgrape leaves. After spraying, the liquid on the stem was air-dried, anda suspension of zoosporangiua of Plasmopara viticola was inoculated byspraying. After inoculation, the plant was first grown for one day at23° C. under high humidity, then further grown for 6 days in the greenhouse, then the control effect was checked.

The areas of a lesion of the plants were visually obserbed. The lesionareas on plants on the plants treated with the present compound 1-003,1-006, 1-058, 1-059, 1-060, 1-063, 1-064, 1-080, 1-098, 1-111, 1-210,1-214, 1-227, 1-252, 2-025, 2-046, 2-062 and 2-078 were not more than10% of the lesion area on a non-treatment plant.

INDUSTRIAL APPLICABILITY

By using the present compound, plant diseases can be controlled.

1. A N-biphenylamide compound of the formula (1):

wherein R¹, R², R³, R⁴ and R⁵ independently represent a hydrogen atom,halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy,C3-C6 haloalkynyloxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C3-C6cycloalkyl, C3-C6 cycloalkoxy, tri(C1-C6 alkyl)silyl or cyano, R⁶represents C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, (C1-C6 alkyl)carbonyl,(C1-C6 haloalkyl)carbonyl, (C2-C6 alkenyl) carbonyl, (C2-C6 haloalkenyl)carbonyl, (C2-C6 alkynyl)carbonyl or (C2-C6 haloalkynyl)carbonyl, R⁷represents a hydrogen atom or C1-C3 alkyl, R⁸ represents a hydrogen atomor C1-C3 alkyl, R⁹ and R¹⁰ independently represents a halogen atom,C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6alkynyl, C2-C6 haloalkynyl, cyano C1-C6 alkyl, C1-C6 alkoxy, C1-C6haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy,C3-C6 haloalkynyloxy, cyano C1-C6 alkoxy, C1-C6 alkylthio, C1-C6haloalkylthio, C3-C6 alkenylthio, C3-C6 alkynylthio, C3-C6 cycloalkyl,C3-C6 cycloalkoxy, (C3-C6 cycloalkyl) C1-C3 alkoxy, C2-C6 alkoxyalkyl,tri(C1-C6 alkyl)silyl or cyano, R¹¹, R¹² and R¹³ independently representa hydrogen atom, halogen atom or C1-C3 alkyl, R¹⁴, R¹⁵, R¹⁶ and R¹⁷independently is a hydrogen atom, halogen atom, C1-C6 alkyl, C1-C6haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 alkenyloxy, C3-C6haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C1-C6 alkylthio,C1-C6 haloalkylthio, C3-C6 cycloalkyl, C3-C6 cycloalkyloxy, tri(C1-C6alkyl)silyl or cyano, X¹ represents an oxygen atom or sulfur atom, X²represents an oxygen atom or sulfur atom.
 2. The N-biphenylamidecompound according to claim 1; wherein X¹ is an oxygen atom in theformula (1).
 3. The N-biphenylamide compound according to claim 1 or 2;wherein X² is an oxygen atom in the formula (1).
 4. The N-biphenylamidecompound according to claim 1; wherein R⁷ is a hydrogen atom in theformula (1).
 5. The N-biphenylamide compound according to claim 1;wherein R⁹ is C1-C6 alkoxy in the formula (1).
 6. The N-biphenylamidecompound according to claim 1; wherein X¹ and X² are oxygen atoms, R⁷ isa hydrogen atom, and R⁹ is C1-C6 alkoxy in the formula (1).
 7. TheN-biphenylamide compound according to claim 1; wherein R¹⁰ is C1-C6alkoxy in the formula (1).
 8. The N-biphenylamide compound according toclaim 1; wherein X¹ and X² are oxygen atoms, R⁷ is a hydrogen atom, R¹⁰is C1-C6 alkoxy in the formula (1).
 9. The N-biphenylamide compoundaccording to claim 1; R⁹ and R¹⁰ are C1-C6 alkoxy in the formula (1).10. The N-biphenylamide compound according to claim 1; X¹ and X² areoxygen atoms, R⁷ is a hydrogen atom, and R⁹ and R¹⁰ are C1-C6 alkoxy inthe formula (1).
 11. A fungicidal composition comprising theN-biphenylamide compound described in claim 1 as an active ingredient.12. A method for controlling plant diseases comprising a step ofapplying the N-biphenylamide compound described in claim 1 to a plant orthe soil.
 13. Use of the N-biphenylamide compound described in claim 1as an active ingredient of fungicidal composition.